476:
287:(resonance structure) with the greatest contribution is drawn. However, the skeletal formula is understood to represent the "real molecule" – that is, the weighted average of all contributing canonical forms. Thus, in cases where two or more canonical forms contribute with equal weight (e.g., in benzene, or a carboxylate anion) and one of the canonical forms is selected arbitrarily, the skeletal formula is understood to depict the true structure, containing equivalent bonds of fractional order, even though the delocalized bonds are depicted as nonequivalent single and double bonds.
1419:
1389:
460:
1437:
1404:
1579:
1559:
1519:
1536:
1599:
1727:
586:
468:
1714:
373:
572:
418:
363:
345:
334:
579:
1658:
1461:
27:
1499:
bonds), in which all carbonâcarbon bonds are of equivalent length and have a bond order of exactly 1.5. For aryl rings in general, the two analogous canonical forms are almost always the primary contributors to the structure, but they are nonequivalent, so one structure may make a slightly greater contribution than the other, and bond orders may differ somewhat from 1.5.
1510:, used to be very common in introductory organic chemistry textbooks and is still frequently used in informal settings. However, because this depiction does not keep track of electron pairs and is unable to show the precise movement of electrons, it has largely been superseded by the Kekuléan depiction in pedagogical and formal academic contexts.
1473:
1844:
American and
European chemists use slightly different conventions for a hashed bond. Whereas most American chemists draw hashed bonds with short hash marks close to the stereocenter and long hash marks further away (in analogy to wedged bonds), most European chemists start with long hash marks close
316:
publications, for instance), these conventions have been nearly universal in the chemical literature since the late 1990s. A few minor conventional variations, especially with respect to the use of stereobonds, continue to exist as a result of differing US, UK and
European practice, or as a matter of
1834:
For instance, the acclaimed 1959 textbook by
Morrison and Boyd (6th edition, 1992) uses the Thiele notation as its standard depiction of the aryl ring, while the 2001 textbook by Clayden, Greeves, Warren, and Wothers (2nd edition, 2012) uses the Kekulé notation throughout and warns students to avoid
1709:
of alkenes. Wavy single bonds are the standard way to represent unknown or unspecified stereochemistry or a mixture of isomers (as with tetrahedral stereocenters). A crossed double-bond has been used sometimes; it is no longer considered an acceptable style for general use but may still be required
1362:
Two atoms can be bonded by sharing more than one pair of electrons. The common bonds to carbon are single, double and triple bonds. Single bonds are most common and are represented by a single, solid line between two atoms in a skeletal formula. Double bonds are denoted by two parallel lines, and
1498:
originally proposed in 1872. As mentioned above, the alternating single and double bonds of "1,3,5-cyclohexatriene" are understood to be a drawing of one of the two equivalent canonical forms of benzene (the one explicitly shown and the one with the opposite pattern of formal single and double
147:
Several other ways of depicting chemical structures are also commonly used in organic chemistry (though less frequently than skeletal formulae). For example, conformational structures look similar to skeletal formulae and are used to depict the approximate positions of atoms in 3D space, as a
160:, also look somewhat similar to skeletal formulae. However, there are slight differences in the conventions used, and the reader needs to be aware of them in order to understand the structural details encoded in the depiction. While skeletal and conformational structures are also used in
193:
bonded to its atoms. Hydrogen is the most common non-carbon atom that is bonded to carbon and, for simplicity, is not explicitly drawn. In addition, carbon atoms are not generally labelled as such directly (i.e. with "C"), whereas heteroatoms are always explicitly noted as such ("N" for
341:
If all four substituents to a tetrahedral carbon are explicitly shown, bonds to the two in-plane substituents still meet at 120°; the other two substituents, however, are usually shown with wedged and dashed bonds (to depict stereochemistry) and subtend a smaller angle of 60â90°.
260:, while a vertex labeled with a formal charge and/or nonbonding electron(s) is understood to have the number of hydrogen atoms required to give the carbon atom these indicated properties. Optionally, acetylenic and formyl hydrogens can be shown explicitly for the sake of clarity.
1849:
has suggested the use of a hashed bond with hash marks of equal length throughout as a compromise but now prefers the
American-style hashed bonds (Brecher, 2006, p. 1905). Some chemists use a thick bond and dotted bond (or hashed bond with equal length hashes) to depict
601:, but represent certain very common substituents or indicate an unspecified member of a group of elements. These are called pseudoelement symbols or organic elements and are treated like univalent "elements" in skeletal formulae. A list of common pseudoelement symbols:
317:
personal preference. As another minor variation between authors, formal charges can be shown with the plus or minus sign in a circle (â, â) or without the circle. The set of conventions that are followed by most authors is given below, along with illustrative examples.
181:
The skeletal structure of an organic compound is the series of atoms bonded together that form the essential structure of the compound. The skeleton can consist of chains, branches and/or rings of bonded atoms. Skeletal atoms other than carbon or hydrogen are called
483:
It does not matter which end of the chain one starts numbering from, as long as consistency is maintained when drawing diagrams. The condensed formula or the IUPAC name will confirm the orientation. Some molecules will become familiar regardless of the orientation.
1654:
chemistry is the use of a filled circle centered on a vertex (sometimes called H-dot/H-dash/H-circle, respectively) for an upward pointing hydrogen atom and two hash marks next to vertex or a hollow circle for a downward pointing hydrogen atom.
295:
Since skeletal structures were introduced in the latter half of the 19th century, their appearance has undergone considerable evolution. The graphical conventions in use today date to the 1980s. Thanks to the adoption of the
475:
209:, as they give the molecule a function. Heteroatoms and functional groups are collectively called "substituents", as they are considered to be a substitute for the hydrogen atom that would be present in the parent
278:
carbons must be indicated explicitly while lone pairs in other cases are optional and are shown only for emphasis. In contrast, formal charges and unpaired electrons on main-group elements are always explicitly
322:
Bonds between sp or sp hybridized carbon or heteroatoms are conventionally represented using 120° angles whenever possible, with the longest chain of atoms following a zigzag pattern unless interrupted by a
1302:
or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction, facilitating multistep organic synthesis.
205:
Heteroatoms and other groups of atoms that give rise to relatively high rates of chemical reactivity, or introduce specific and interesting characteristics in the spectra of compounds are called
1598:
459:
1056:. However, since the anisyl group is monovalent, while the actinides are usually divalent, trivalent, or even higher valency, ambiguity rarely, if ever, arises in practice.
1770:
To prevent a 'kink' from emerging and causing a structure to take up too much vertical space on a page, the IUPAC (Brecher, 2008, p. 352) makes an exception for long chain
1761:
This term is ambiguous, because "Kekulé structure" also refers to Kekulé's famous proposal of a hexagon of alternating single and double bonds for the structure of benzene.
1825:
In this gallery, double bonds have been shown in red and triple bonds in blue. This was added for clarity â multiple bonds are not normally coloured in skeletal formulae.
2138:
1846:
1418:
1388:
542:
OH, for instance, the hydrogen atom bonded to oxygen is denoted by the symbol H, whereas the hydrogen atoms which are bonded to carbon atoms are not shown directly.
256:
Hydrogen atoms attached to carbon are implied. An unlabeled vertex is understood to represent a carbon attached to the number of hydrogens required to satisfy the
958:. However, argon is inert under all usual conditions encountered in organic chemistry, so the use of Ar to represent an aryl substituent never causes confusion.)
263:
Hydrogen atoms attached to a heteroatom are shown explicitly. The heteroatom and hydrogen atoms attached thereto are usually shown as a single group (e.g., OH, NH
241:
Carbon atoms are represented by the vertices (intersections or termini) of line segments. For clarity, methyl groups are often explicitly written out as Me or CH
1535:
440:
appears to have only one bond, so there must also be three hydrogens bonded to it, in order to make its total number of bonds four. The carbon atom labelled C
1816:
NH in the middle of a chain), some authors allow the group's formula to be stacked vertically whereas others draw an explicit vertical bond within the group.
549:
group is most often written âOH instead of âOâH. These bonds are sometimes drawn out in full in order to accentuate their presence when they participate in
1328:
1436:
1403:
1578:
1558:
370:
Carbo- and heterocycles (3- to 8-membered) are generally represented as regular polygons; larger ring sizes tend to be represented by concave polygons.
267:) without explicitly showing the hydrogenâheteroatom bond. Heteroatoms with simple alkyl or aryl substituents, like methoxy (OMe) or dimethylamino (NMe
1502:
An alternate representation that emphasizes this delocalization uses a circle, drawn inside the hexagon of single bonds, to represent the delocalized
352:
The linear geometry at sp hybridized atoms is normally depicted by line segments meeting at 180°. Where this involves two double bonds meeting (an
2292:
755:. However, since the propyl group is monovalent, while praseodymium is nearly always trivalent, ambiguity rarely, if ever, arises in practice.
327:
double bond. Unless all four substituents are explicit, this is true even when stereochemistry is being depicted using wedged or dashed bonds (
1283:. However, tennessine is too unstable to ever be encountered in organic chemistry, so the use of Ts to represent tosyl never causes confusion)
2131:
2003:
1106:. However, actinium is almost never encountered in organic chemistry, so the use of Ac to represent the acetyl group never causes confusion)
3064:
1741:
are generally denoted by dotted or dashed lines. In other contexts, dashed lines may also represent partially formed or broken bonds in a
1374:
exist. In these cases, a combination of solid and dashed lines indicate the integer and non-integer parts of the bond order, respectively.
1782:
double bond within them to be depicted with 150° angles, so that the zigzags on either side of the double bond can propagate horizontally.
619:
1644:
Hashed wedges or dashed lines (thick or thin) represent bonds that point into the plane of the paper or screen, away from the observer.
3054:
2997:
2603:
1900:
2259:
467:
105:
that make up the molecule. It is represented in two dimensions, as on a piece of paper. It employs certain conventions to represent
2124:
380:
Atoms in a group are ordered so that the bond emanates from the atom that is directly attached to the skeleton. For example, the
2608:
313:
545:
Lines representing heteroatom-hydrogen bonds are usually omitted for clarity and compactness, so a functional group like the
237:). In fact, skeletal formulae can be thought of as abbreviated Lewis structures that observe the following simplifications:
1395:
2316:
1661:
A small filled circle represented an upward pointing hydrogen, while two hash marks represented a downward pointing one.
221:
As in Lewis structures, covalent bonds are indicated by line segments, with a doubled or tripled line segment indicating
3182:
2598:
680:
Z for conjugating electron-withdrawing groups (in the related MLXZ notation, Z represents a zero-electron donor ligand;
2285:
2527:
1845:
to the stereocenter that gradually become shorter moving away (in analogy to perspective drawing). In the past, the
3177:
3172:
2031:
1936:
309:
284:
2351:
1647:
Wavy lines represent either unknown stereochemistry or a mixture of the two possible stereoisomers at that point.
1507:
305:
2376:
2371:
2336:
2301:
1792:
1518:
1076:
1062:
161:
565:
2947:
2563:
2499:
2386:
2278:
2841:
2654:
2578:
2396:
963:
453:
141:
2942:
1641:
Solid wedges represent bonds that point out of the plane of the paper or screen, towards the observer.
3121:
3012:
2836:
2786:
2694:
2679:
2623:
2588:
2484:
2381:
2356:
2223:
2078:
1542:
1494:
is generally depicted as a hexagon with alternating single and double bonds, much like the structure
449:
2613:
3101:
2856:
2791:
2628:
2583:
2489:
2439:
2434:
2228:
2023:
1699:
165:
1726:
3141:
2801:
2796:
2750:
2740:
2674:
2366:
2341:
2331:
2183:
2048:
1932:"Graphical representation standards for chemical structure diagrams (IUPAC Recommendations 2008)"
561:
550:
157:
153:
90:
78:
3007:
585:
479:
The 3d ball representation of hexane, with carbon (black) and hydrogen (white) shown explicitly.
2912:
3136:
3086:
3059:
2987:
2866:
2846:
2689:
2494:
2391:
2196:
2173:
2168:
2066:
1999:
1965:
1896:
1795:) or polycyclic molecules that cannot be drawn 'flat' without significant distortion (such as
1692:
1618:
149:
133:
86:
3146:
3131:
3126:
3106:
2957:
2932:
2896:
2891:
2826:
2760:
2664:
2573:
2568:
2558:
2532:
2406:
2346:
2321:
2153:
2107:
2086:
2040:
1983:
1955:
1945:
1742:
1672:
1495:
1307:
1299:
896:
206:
117:
74:
1812:
In cases where the atom has bonds coming from both the left and right (such as a secondary
3151:
3091:
3002:
2927:
2871:
2821:
2464:
2361:
2249:
2215:
2191:
1610:
1526:
834:
598:
557:
493:
445:
121:
51:
2270:
2082:
1713:
444:
has two bonds to other carbons and is therefore bonded to two hydrogen atoms as well. A
372:
3116:
3081:
3022:
2977:
2876:
2861:
2755:
2730:
2684:
2638:
2633:
2469:
2401:
2024:"Graphical representation of stereochemical configuration (IUPAC Recommendations 2006)"
1688:
1155:
853:
508:, and so forth. In the context of organic chemistry, these atoms are commonly known as
230:
31:
3166:
3076:
2962:
2886:
2851:
2831:
2735:
2699:
2553:
2537:
2522:
2326:
1991:
1987:
1916:
1738:
1635:
1321:
1149:
611:
137:
43:
2052:
136:, partly because they are relatively quick and simple to draw, and also because the
3111:
3071:
2992:
2972:
2937:
2922:
2816:
2811:
2781:
2659:
2233:
1676:
1668:
1168:
1003:
752:
720:
664:
639:
or ligands (in the related MLXZ notation, L represents a two-electron donor ligand)
571:
417:
362:
344:
333:
47:
35:
1671:
who in 1932 used solid thick lines and dotted lines in a publication. The modern
3096:
3044:
2982:
2952:
2881:
2806:
2776:
2714:
2669:
1791:
Smaller rings may also be drawn as concave to show stereochemistry (such as the
1731:
1657:
1606:
1341:
1083:
949:
917:
777:
726:
675:
578:
381:
226:
222:
210:
190:
1650:
An obsolescent depiction of hydrogen stereochemistry that used to be common in
2967:
2745:
2709:
2704:
2454:
1800:
1775:
1503:
1371:
1280:
924:
257:
250:
183:
39:
2069:(2013). "The Historical Origins of Stereochemical Line and Wedge Symbolism".
1969:
3049:
3017:
2618:
2593:
2474:
2459:
2044:
1950:
1931:
1460:
1263:
1220:
1159:
904:
890:
877:
770:
688:
116:
An early form of this representation was first developed by organic chemist
2116:
463:
The skeletal formula of hexane, with carbons number one and three labelled
124:
of molecules and their valence electrons. Hence they are sometimes termed
26:
2444:
1424:
1409:
1286:
1213:
1209:
1190:
1183:
1179:
1123:
1116:
1103:
1068:
1053:
818:
682:
in unrelated usage, Z is also an abbreviation for the carboxybenzyl group
546:
497:
357:
297:
246:
195:
110:
98:
82:
20:
2917:
2429:
1796:
1680:
1651:
1491:
1367:
1200:
1112:
1043:
1018:
992:
980:
794:
713:
695:
668:
615:
531:
452:(bottom) of the actual molecular structure of hexane, as determined by
404:
275:
2090:
1960:
466:
416:
371:
361:
343:
332:
2254:
1428:
1097:
974:
935:
871:
863:
742:
636:
513:
505:
501:
433:
353:
233:
associated with each atom (although lone pairs are usually optional,
199:
106:
1835:
using the Thiele notation when writing mechanisms (p. 144, 2nd ed.).
403:, depending on the placement of the bond. In contrast, the isomeric
120:, while the modern form is closely related to and influenced by the
1199:(Ns was the chemical symbol for nielsbohrium, but that was renamed
2424:
1813:
1725:
1712:
1656:
1517:
1472:
1270:
955:
709:
647:
25:
492:
All atoms that are not carbon or hydrogen are signified by their
1854:
and a wedged bond and hashed bond with unequal hashes to depict
716:
group (Alk can be used to unambiguously indicate an alkyl group)
2274:
2120:
656:, when the identities of the ligands are unknown or irrelevant)
2449:
1009:
895:
Warning: Organometallic chemists often use Np for the related
1630:
The relevant chemical bonds can be depicted in several ways:
560:(middle) and its ball-and-stick model (bottom) of the actual
556:
Shown below for comparison are a skeletal formula (top), its
148:
perspective drawing. Other types of representation, such as
584:
577:
570:
474:
458:
1522:
Different depictions of chemical bonds in skeletal formulas
983:
group; However, old literature may use Bz for benzyl group.
564:
of the ethanol molecule in the gas phase, as determined by
140:
notation used for discussions of reaction mechanisms and
19:"Skeletal structure" redirects here. For other uses, see
1175:-bromobenzenesulfonyl) group; OBs is the brosylate group
113:
atoms, which are the most common in organic chemistry.
229:, respectively. Likewise, skeletal formulae indicate
1998:(1st ed.). Oxford University Press. p. 27.
1067:
Cp was the symbol for cassiopeium, a former name for
1667:
An early use of this notation can be traced back to
3035:
2905:
2769:
2723:
2647:
2546:
2515:
2508:
2415:
2309:
2242:
2214:
2182:
2161:
2152:
1683:, and extensively popularised in the 1959 textbook
271:), are sometimes shown in the same way, by analogy.
667:(in some contexts, E is also used to indicate any
1730:Dashed lines (green) to show hydrogen bonding in
1130:-butylcarbonyl) group; OPiv is the pivalate group
168:, the conventions employed also differ somewhat.
1870:The IUPAC now strongly deprecates this notation.
1363:triple bonds are shown by three parallel lines.
1915:IUPAC Recommendations 1999, Revised Section F:
1379:Examples of multiple bonds in skeletal formulae
436:(top) is shown below. The carbon atom labeled C
132:. Skeletal formulae have become ubiquitous in
81:that serves as a shorthand representation of a
1529:is conveniently denoted in skeletal formulae:
1340:TMS, TBDMS, TES, TBDPS, TIPS, ... for various
650:atom ( is used to indicate a ligated metal, ML
249:carbons are frequently represented by a heavy
2286:
2132:
2017:
2015:
1609:, indicating a mixture of two stereoisomers:
1212:(trifluoromethanesulfonyl) group; OTf is the
1034:the former symbol is derived from the synonym
1032:Tipp for the 2,4,6-triisopropylphenyl group (
283:In the standard depiction of a molecule, the
8:
471:The Lewis structure of hexane, for reference
1861:; most others do not make this distinction.
622:, X represents a one-electron donor ligand)
2512:
2293:
2279:
2271:
2158:
2139:
2125:
2117:
1893:General, Organic, and Biological Chemistry
1366:In more advanced theories of bonding, non-
1337:Troc for the trichloroethoxycarbonyl group
903:Câ. Np is also the symbol for the element
1959:
1949:
1484:Represenatations of aromatic benzene ring
597:There are also symbols that appear to be
526:Any hydrogen atoms bonded to heteroatoms
189:The skeleton has hydrogen and/or various
1506:. This style, based on one proposed by
1152:in nucleophilic substitution reactions.
988:Dipp for the 2,6-diisopropylphenyl group
101:of a molecule, which is composed of the
38:, featuring skeletal representations of
1883:
1754:
1531:
1384:
1279:(Ts is also the symbol for the element
1102:(Ac is also the symbol for the element
954:(Ar is also the symbol for the element
488:Explicit heteroatoms and hydrogen atoms
1478:Kekulé style: alternating double bonds
751:Pr is also the symbol for the element
1353:THP for the 2-tetrahydropyranyl group
943:Aromatic and unsaturated substituents
432:For example, the skeletal formula of
360:), the bonds are separated by a dot.
7:
1638:in the plane of the paper or screen.
1442:Hex-1-yne has a terminal triple bond
1334:Alloc for the allyloxycarbonyl group
1182:(methanesulfonyl) group; OMs is the
1139:NPhth for the phthalimide-1-yl group
1052:An is also the symbol for a generic
1679:to represent the structure of high
876:although Am is also the symbol for
1223:(nonafluorobutanesulfonyl) group,
428:Implicit carbon and hydrogen atoms
291:Contemporary graphical conventions
16:Representation method in chemistry
14:
1347:PMB for the 4-methoxybenzyl group
1133:Bt for the 1-benzotriazolyl group
1675:were introduced in the 1940s by
1597:
1577:
1557:
1534:
1471:
1459:
1435:
1417:
1402:
1387:
1350:MOM for the methoxymethyl group
1162:groups for further information.
979:not to be confused with Bz for
314:Gesellschaft Deutscher Chemiker
144:can be readily superimposed.
93:. A skeletal formula shows the
1012:for phenyl has been in decline
1:
2317:Biological data visualization
2071:Journal of Chemical Education
1918:Replacement of Skeletal Atoms
1698:Skeletal formulae can depict
1197:-nitrobenzenesulfonyl) group
1136:Im for the 1-imidazolyl group
1793:conformations of cyclohexane
1466:Thiele style: unified circle
456:, are shown for comparison.
30:The skeletal formula of the
1891:Stoker, H. Stephen (2012).
1205:; ONs is the nosylate group
1148:Sulfonate esters are often
1077:pentamethylcyclopentadienyl
523:héteros, meaning "other").
3199:
2357:Mathematical visualization
2032:Pure and Applied Chemistry
2022:Brecher, Jonathan (2006).
1937:Pure and Applied Chemistry
1930:Brecher, Jonathan (2008).
1591:)-2-chloro-2-fluoropentane
1571:)-2-chloro-2-fluoropentane
1551:)-2-chloro-2-fluoropentane
1412:has a terminal double bond
1394:Hex-3-ene has an internal
817:often italicized) for the
310:Royal Society of Chemistry
18:
2352:Information visualization
2337:Educational visualization
2108:Drawing organic molecules
1895:(6th ed.). Cengage.
1429:carbonâcarbon triple bond
1396:carbonâcarbon double bond
1144:Sulfonyl/sulfonate groups
306:American Chemical Society
213:of the organic compound.
2528:Charles-René de Fourcroy
2377:Scientific visualization
2304:of technical information
1852:relative stereochemistry
1329:fluorenylmethoxycarbonyl
599:chemical element symbols
89:and some details of its
2162:Non-structural formulas
2147:Molecular visualization
2045:10.1351/pac200678101897
1951:10.1351/pac200880020277
1673:solid and hashed wedges
1277:toluenesulfonyl) group
142:electron delocalization
130:LewisâKekulĂ© structures
77:is a type of molecular
2948:Christopher R. Johnson
2500:Technical illustration
2387:Software visualization
1735:
1718:
1717:Alkene stereochemistry
1710:by computer software.
1662:
1634:Solid lines represent
1523:
870:Am for the synonymous
589:
582:
575:
566:microwave spectroscopy
496:, for instance Cl for
480:
472:
464:
421:
376:
366:
348:
337:
304:industry standard (by
300:software package as a
54:
2842:Lawrence J. Rosenblum
2655:Edward Walter Maunder
2579:Charles Joseph Minard
2397:User interface design
2372:Product visualization
1729:
1716:
1660:
1521:
618:atom (in the related
593:Pseudoelement symbols
588:
581:
574:
530:drawn explicitly. In
478:
470:
462:
454:X-ray crystallography
420:
375:
365:
347:
336:
29:
3122:Scientific modelling
3097:Information graphics
2837:Clifford A. Pickover
2787:William S. Cleveland
2695:Henry Norris Russell
2680:Howard G. Funkhouser
2624:Florence Nightingale
2589:Francis Amasa Walker
2485:Statistical graphics
2407:Volume visualization
2382:Social visualization
2224:Ball-and-stick model
1605:Skeletal formula of
1585:Skeletal formula of
1565:Skeletal formula of
1543:Ball-and-stick model
1154:See the articles on
450:ball-and-stick model
3183:Chemical structures
3102:Information science
3065:in computer science
2857:Sheelagh Carpendale
2792:George G. Robertson
2629:Karl Wilhelm Pohlke
2564:André-Michel Guerry
2440:Graph of a function
2435:Engineering drawing
2229:Space-filling model
2184:Structural formulas
2083:2013JChEd..90..676J
1046:group, usually the
1021:group, usually the
551:reaction mechanisms
166:inorganic chemistry
3142:Volume cartography
2906:Early 21st century
2802:Catherine Plaisant
2797:Bruce H. McCormick
2751:Mary Eleanor Spear
2741:Arthur H. Robinson
2675:Arthur Lyon Bowley
2648:Early 20th century
2495:Technical drawings
2367:Molecular graphics
2342:Flow visualization
2332:Data visualization
2067:Jensen, William B.
1774:-olefins (such as
1736:
1719:
1663:
1524:
1115:group; OBz is the
712:group or even any
590:
583:
576:
481:
473:
465:
422:
377:
367:
349:
338:
158:Fischer projection
154:Haworth projection
95:skeletal structure
91:molecular geometry
79:structural formula
63:line-angle formula
55:
3178:Chemical formulas
3173:Organic chemistry
3160:
3159:
3137:Visual perception
3087:Graphic organizer
3060:Computer graphics
3031:
3030:
3013:Martin Wattenberg
2988:Hanspeter Pfister
2943:Martin Krzywinski
2867:Jock D. Mackinlay
2847:Thomas A. DeFanti
2770:Late 20th century
2690:Ejnar Hertzsprung
2392:Technical drawing
2268:
2267:
2210:
2209:
2197:Condensed formula
2174:Molecular formula
2169:Empirical formula
2154:Chemical formulas
2091:10.1021/ed200177u
2039:(10): 1897â1970.
2005:978-0-19-850346-0
1996:Organic Chemistry
1986:; Greeves, Nick;
1984:Clayden, Jonathan
1693:George S. Hammond
1685:Organic Chemistry
1490:In recent years,
1294:Protecting groups
1091:Functional groups
519:comes from Greek
207:functional groups
150:Newman projection
134:organic chemistry
126:Kekulé structures
71:shorthand formula
67:bond-line formula
3190:
3147:Volume rendering
3132:Visual analytics
3127:Spatial analysis
3107:Misleading graph
2958:David McCandless
2933:Gordon Kindlmann
2897:Alfred Inselberg
2892:Leland Wilkinson
2827:Michael Friendly
2761:Howard T. Fisher
2724:Mid 20th century
2665:W. E. B. Du Bois
2569:William Playfair
2559:Adolphe Quetelet
2533:Joseph Priestley
2516:Pre-19th century
2513:
2480:Skeletal formula
2347:Geovisualization
2322:Chemical imaging
2295:
2288:
2281:
2272:
2216:Molecular models
2202:Skeletal formula
2159:
2141:
2134:
2127:
2118:
2095:
2094:
2063:
2057:
2056:
2028:
2019:
2010:
2009:
1980:
1974:
1973:
1963:
1953:
1927:
1921:
1913:
1907:
1906:
1888:
1871:
1868:
1862:
1842:
1836:
1832:
1826:
1823:
1817:
1810:
1804:
1789:
1783:
1778:), allowing the
1768:
1762:
1759:
1743:transition state
1601:
1581:
1561:
1538:
1475:
1463:
1439:
1427:has an internal
1421:
1406:
1391:
1300:protecting group
1261:
1260:
1259:
1251:
1250:
1242:
1241:
1233:
1232:
1063:cyclopentadienyl
1054:actinoid element
414:
410:
402:
394:
245:, while (hetero)
75:organic compound
59:skeletal formula
3198:
3197:
3193:
3192:
3191:
3189:
3188:
3187:
3163:
3162:
3161:
3156:
3152:Information art
3092:Imaging science
3037:
3027:
3008:Fernanda Viégas
3003:Moritz Stefaner
2928:Jessica Hullman
2901:
2872:Alan MacEachren
2822:Ben Shneiderman
2765:
2719:
2643:
2542:
2504:
2417:
2411:
2362:Medical imaging
2305:
2299:
2269:
2264:
2250:Molecular graph
2238:
2206:
2192:Lewis structure
2178:
2148:
2145:
2112:chemguide.co.uk
2104:
2099:
2098:
2065:
2064:
2060:
2026:
2021:
2020:
2013:
2006:
1982:
1981:
1977:
1929:
1928:
1924:
1914:
1910:
1903:
1890:
1889:
1885:
1880:
1875:
1874:
1869:
1865:
1859:stereochemistry
1843:
1839:
1833:
1829:
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1811:
1807:
1790:
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1592:
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1566:
1562:
1553:
1552:
1546:
1539:
1527:Stereochemistry
1516:
1514:Stereochemistry
1508:Johannes Thiele
1488:
1487:
1486:
1485:
1481:
1480:
1479:
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1227:
1226:
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1146:
1093:
945:
902:
705:
655:
634:
607:
605:General symbols
595:
558:Lewis structure
541:
537:
494:chemical symbol
490:
446:Lewis structure
443:
439:
430:
425:
412:
408:
400:
396:
393:
389:
387:
293:
270:
266:
244:
219:
217:Basic structure
179:
174:
122:Lewis structure
52:stereochemistry
24:
17:
12:
11:
5:
3196:
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3180:
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3117:Patent drawing
3114:
3109:
3104:
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3089:
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3082:Graphic design
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3057:
3052:
3047:
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3039:
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3023:Hadley Wickham
3020:
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3010:
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2990:
2985:
2980:
2978:Tamara Munzner
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2877:David Goodsell
2874:
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2862:Cynthia Brewer
2859:
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2849:
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2839:
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2763:
2758:
2756:Edgar Anderson
2753:
2748:
2743:
2738:
2733:
2731:Jacques Bertin
2727:
2725:
2721:
2720:
2718:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2685:John B. Peddle
2682:
2677:
2672:
2667:
2662:
2657:
2651:
2649:
2645:
2644:
2642:
2641:
2639:Francis Galton
2636:
2634:Toussaint Loua
2631:
2626:
2621:
2616:
2614:Georg von Mayr
2611:
2606:
2604:Matthew Sankey
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2550:
2548:
2544:
2543:
2541:
2540:
2535:
2530:
2525:
2519:
2517:
2510:
2506:
2505:
2503:
2502:
2497:
2492:
2487:
2482:
2477:
2472:
2470:Sankey diagram
2467:
2462:
2457:
2452:
2447:
2442:
2437:
2432:
2427:
2421:
2419:
2413:
2412:
2410:
2409:
2404:
2402:Visual culture
2399:
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2240:
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2165:
2163:
2156:
2150:
2149:
2146:
2144:
2143:
2136:
2129:
2121:
2115:
2114:
2103:
2102:External links
2100:
2097:
2096:
2077:(5): 676â677.
2058:
2011:
2004:
1992:Wothers, Peter
1988:Warren, Stuart
1975:
1944:(2): 277â410.
1922:
1908:
1902:978-1133103943
1901:
1882:
1881:
1879:
1876:
1873:
1872:
1863:
1837:
1827:
1818:
1805:
1784:
1763:
1753:
1752:
1750:
1747:
1739:Hydrogen bonds
1723:
1722:Hydrogen bonds
1720:
1689:Donald J. Cram
1665:
1664:
1648:
1645:
1642:
1639:
1628:
1627:
1604:
1603:
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1408:
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1399:
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1383:
1382:
1378:
1377:
1376:
1359:
1358:Multiple bonds
1356:
1355:
1354:
1351:
1348:
1345:
1338:
1335:
1332:
1325:
1314:
1311:butoxycarbonyl
1295:
1292:
1291:
1290:
1267:
1256:
1247:
1238:
1229:
1217:
1206:
1187:
1176:
1150:leaving groups
1145:
1142:
1141:
1140:
1137:
1134:
1131:
1120:
1109:
1092:
1089:
1088:
1087:
1080:
1073:
1059:
1040:
1026:
1015:
996:
989:
986:
967:
964:heteroaromatic
960:
944:
941:
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939:
928:
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822:
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319:
292:
289:
285:canonical form
281:
280:
274:Lone pairs on
272:
268:
264:
261:
254:
242:
231:formal charges
227:triple bonding
218:
215:
178:
175:
173:
170:
162:organometallic
103:skeletal atoms
32:antidepressant
15:
13:
10:
9:
6:
4:
3:
2:
3195:
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3077:Graph drawing
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3006:
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3001:
2999:
2998:Claudio Silva
2996:
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2989:
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2963:Mauro Martino
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2887:Michael Maltz
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2855:
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2852:George Furnas
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2832:Howard Wainer
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2736:Rudolf Modley
2734:
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2609:Charles Booth
2607:
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2584:Luigi Perozzo
2582:
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2574:August Kekulé
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2554:Charles Dupin
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2538:Gaspard Monge
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2523:Edmond Halley
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1322:carboxybenzyl
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1305:
1304:
1303:
1301:
1293:
1288:
1285:; OTs is the
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1265:
1262:; ONf is the
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923:Ad for the 1-
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915:
911:
908:
906:
898:
892:
888:
884:
881:
879:
873:
869:
865:
861:
858:
856:
851:
849:
845:
842:
839:
837:
832:
830:
826:
823:
820:
816:
812:
810:
806:
803:
800:
798:
792:
790:
786:
782:
779:
775:
772:
768:
766:
762:
759:
756:
754:
748:
746:
740:
738:
734:
730:
728:
724:
722:
718:
715:
711:
707:
706:
702:
697:
693:
690:
686:
683:
679:
677:
673:
670:
666:
662:
658:
654:
649:
645:
641:
638:
633:
628:
624:
621:
620:MLXZ notation
617:
613:
609:
608:
604:
602:
600:
592:
587:
580:
573:
569:
567:
563:
559:
554:
552:
548:
543:
533:
529:
524:
522:
518:
515:
511:
507:
503:
499:
495:
487:
485:
477:
469:
461:
457:
455:
451:
448:(middle) and
447:
435:
427:
419:
406:
405:nitrite group
383:
379:
374:
369:
364:
359:
355:
351:
346:
340:
335:
330:
326:
321:
320:
318:
315:
311:
307:
303:
299:
290:
288:
286:
277:
273:
262:
259:
255:
252:
248:
240:
239:
238:
236:
232:
228:
224:
216:
214:
212:
208:
203:
201:
197:
192:
187:
185:
176:
171:
169:
167:
163:
159:
155:
151:
145:
143:
139:
135:
131:
127:
123:
119:
118:August Kekulé
114:
112:
108:
104:
100:
96:
92:
88:
84:
80:
76:
72:
68:
64:
60:
53:
49:
48:phenyl groups
45:
41:
37:
33:
28:
22:
3112:Neuroimaging
3072:CPK coloring
3055:Color coding
2993:Hans Rosling
2973:Miriah Meyer
2938:Aaron Koblin
2923:Jeffrey Heer
2817:Edward Tufte
2812:Pat Hanrahan
2782:Nigel Holmes
2660:Otto Neurath
2599:Oliver Byrne
2547:19th century
2479:
2234:CPK coloring
2201:
2111:
2074:
2070:
2061:
2036:
2030:
1995:
1978:
1941:
1935:
1925:
1917:
1911:
1892:
1886:
1866:
1858:
1855:
1851:
1840:
1830:
1821:
1808:
1787:
1779:
1771:
1766:
1757:
1737:
1704:
1700:
1697:
1684:
1677:Giulio Natta
1669:Richard Kuhn
1666:
1629:
1620:
1612:
1588:
1568:
1548:
1525:
1501:
1489:
1365:
1361:
1317:
1308:
1306:Boc for the
1297:
1278:
1274:
1198:
1194:
1172:
1153:
1147:
1127:
1122:Piv for the
1101:
1075:Cp* for the
1066:
1051:
1047:
1036:
1033:
1029:
1022:
1017:Tol for the
1007:
1004:phenyl group
999:
991:Mes for the
978:
973:Bzl for the
970:
962:Het for any
953:
952:substituent
934:Trt for the
931:
916:Chx for the
913:
894:
889:Neo for the
886:
875:
867:
854:
850:
847:
843:
835:
831:
828:
824:
814:
811:
808:
804:
796:
791:
788:
784:
776:All for the
767:
764:
760:
753:praseodymium
750:
744:
739:
736:
732:
721:methyl group
703:Alkyl groups
681:
665:electrophile
660:
652:
646:Met for any
643:
631:
626:
596:
562:3D structure
555:
544:
527:
525:
520:
516:
509:
491:
482:
431:
328:
324:
301:
294:
282:
234:
220:
204:
191:substituents
188:
180:
172:The skeleton
146:
138:curved arrow
129:
125:
115:
102:
94:
70:
66:
62:
58:
56:
36:escitalopram
3045:Cartography
2983:Ade Olufeko
2953:Manuel Lima
2882:Kwan-Liu Ma
2807:Stuart Card
2777:Borden Dent
2715:Erwin Raisz
2670:Henry Gantt
1732:acetic acid
1607:amphetamine
1342:silyl ether
1219:Nf for the
1208:Tf for the
1189:Ns for the
1178:Ms for the
1167:Bs for the
1111:Bz for the
1096:Ac for the
1084:vinyl group
1082:Vi for the
1061:Cp for the
1042:An for the
1008:the use of
966:substituent
948:Ar for any
899:group, PhMe
862:Pn for the
852:Bu for the
833:Bu for the
793:Bu for the
778:allyl group
769:Pr for the
741:Pr for the
727:ethyl group
725:Et for the
719:Me for the
676:nucleophile
674:Nu for any
663:El for any
610:X for any (
510:heteroatoms
407:is denoted
388:is denoted
382:nitro group
211:hydrocarbon
184:heteroatoms
177:Terminology
44:triple bond
40:heteroatoms
3167:Categories
2968:John Maeda
2746:John Tukey
2710:Harry Beck
2705:Fritz Kahn
2455:Photograph
2243:Other ways
1961:10092/2052
1878:References
1801:adamantane
1776:oleic acid
1504:pi orbital
1372:bond order
1370:values of
1320:Z for the
1281:tennessine
1086:(uncommon)
1002:Ï for the
918:cyclohexyl
780:(uncommon)
708:R for any
258:octet rule
251:center dot
198:, "O" for
3050:Chartjunk
3018:Bang Wong
2913:Polo Chau
2619:John Snow
2594:John Venn
2475:Schematic
2460:Pictogram
1970:1365-3075
1425:Hex-3-yne
1410:Hex-1-ene
1264:nonaflate
1160:sulfonate
925:adamantyl
905:neptunium
891:neopentyl
878:americium
836:secondary
771:isopropyl
689:deuterium
504:, Na for
329:see below
235:see below
3036:Related
2445:Ideogram
2053:97528124
1994:(2001).
1856:absolute
1681:polymers
1287:tosylate
1221:nonaflyl
1214:triflate
1184:mesylate
1156:sulfonyl
1117:benzoate
1104:actinium
1069:lutetium
1050:isomer (
950:aromatic
855:tertiary
819:isobutyl
747:) propyl
671:element)
547:hydroxyl
500:, O for
498:chlorine
358:cumulene
302:de facto
298:ChemDraw
247:cumulene
202:, etc.)
196:nitrogen
111:hydrogen
99:skeleton
83:molecule
21:Skeleton
2918:Ben Fry
2430:Diagram
2079:Bibcode
1797:tropane
1707:isomers
1652:steroid
1492:benzene
1368:integer
1269:Ts for
1210:triflyl
1201:bohrium
1124:pivalyl
1113:benzoyl
1065:group (
998:Ph, Ί,
993:mesityl
981:benzoyl
977:group (
897:neophyl
893:group (
874:group,
866:group (
799:) butyl
749:group (
714:organyl
696:tritium
669:p-block
616:halogen
532:ethanol
517:hetero-
276:carbene
87:bonding
3038:topics
2509:People
2416:Image
2310:Fields
2255:SMILES
2051:
2002:
1968:
1899:
1496:Kekulé
1344:groups
1169:brosyl
1100:group
1098:acetyl
1044:anisyl
1037:isityl
1025:isomer
975:benzyl
936:trityl
864:pentyl
797:normal
745:normal
694:T for
687:D for
637:ligand
635:for a
612:pseudo
521:áŒÏΔÏÎżÏ
514:prefix
506:sodium
502:oxygen
434:hexane
354:allene
312:, and
279:shown.
223:double
200:oxygen
107:carbon
73:of an
2490:Table
2425:Chart
2418:types
2260:InChl
2110:from
2049:S2CID
2027:(PDF)
1847:IUPAC
1814:amine
1749:Notes
1705:trans
1636:bonds
1331:group
1324:group
1313:group
1289:group
1271:tosyl
1266:group
1216:group
1203:, Bh)
1191:nosyl
1186:group
1180:mesyl
1119:group
1079:group
1019:tolyl
995:group
956:argon
938:group
927:group
920:group
859:group
857:butyl
840:group
838:butyl
821:group
801:group
773:group
735:-Pr,
710:alkyl
648:metal
512:(the
34:drug
2465:Plot
2000:ISBN
1966:ISSN
1897:ISBN
1799:and
1703:and
1691:and
1617:and
1316:Cbz
1158:and
1048:para
1023:para
872:amyl
846:-Bu
827:-Bu
813:Bu (
807:-Bu
787:-Bu
783:Bu,
763:-Pr
731:Pr,
413:ONOâ
409:âONO
164:and
109:and
57:The
50:and
42:, a
2450:Map
2087:doi
2041:doi
1956:hdl
1946:doi
1780:cis
1772:cis
1701:cis
1687:by
1545:of
1234:(CF
1028:Is
1010:phi
969:Bn
930:Tr
912:Cy
885:Np
698:(H)
691:(H)
534:, C
528:are
411:or
395:or
390:âNO
356:or
331:).
325:cis
225:or
156:or
128:or
97:or
85:'s
69:or
3169::
2085:.
2075:90
2073:.
2047:.
2037:78
2035:.
2029:.
2014:^
1990:;
1964:.
1954:.
1942:80
1940:.
1934:.
1803:).
1745:.
1695:.
1623:)-
1615:)-
1318:or
1309:t-
1298:A
1275:p-
1252:SO
1225:CF
1030:or
1000:or
971:or
932:or
914:or
887:or
868:or
848:or
829:or
809:or
789:or
765:or
737:or
684:.)
661:or
659:E
644:or
642:M
627:or
625:L
568:.
553:.
415:.
401:Nâ
384:NO
308:,
186:.
152:,
65:,
61:,
46:,
2294:e
2287:t
2280:v
2140:e
2133:t
2126:v
2093:.
2089::
2081::
2055:.
2043::
2008:.
1972:.
1958::
1948::
1905:.
1734:.
1621:S
1619:(
1613:R
1611:(
1589:S
1587:(
1569:R
1567:(
1549:R
1547:(
1273:(
1257:2
1248:3
1243:)
1239:2
1230:3
1195:p
1193:(
1173:p
1171:(
1128:t
1126:(
1108:;
1072:)
1058:)
1039:)
1014:)
1006:(
985:)
909:)
907:.
901:2
882:)
880:.
844:t
825:s
815:i
805:i
795:(
785:n
761:i
757:)
743:(
733:n
653:n
632:n
629:L
614:)
540:5
538:H
536:2
442:3
438:1
399:2
397:O
392:2
386:2
269:2
265:2
253:.
243:3
23:.
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