699:
1203:. This flexibility is anisotropic; to bend HCB to 180° you must stress the face of the crystal. Another example of a flexible molecular solid is 2-(methylthio)nicotinic acid (MTN). MTN is flexible due to its strong hydrogen bonding and π-π interactions creating a rigid set of dimers that dislocate along the alignment of their terminal methyls. When stressed on the face this crystal will bend 180°. Note, not all ductile molecular solids bend 180°, and some may have more than one bending face.
637:
595:
708:
715:
509:
546:
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charge (δ = -0.59) on the cyano- moiety on TCNQ at room temperature. For reference, a completely charged molecule δ = ±1. This partial negative charge leads to a strong interaction with the thio- moiety of the TTF. The strong interaction leads to favorable alignment of these functional groups adjacent to each other in the solid state. While π-π interactions cause the TTF and TCNQ to stack in separate columns.
446:
38:
722:
692:
514:
naphthalene molecules and quadrupole. (b) A 3D representation of the quadrupole from two naphthalene molecules interacting. (c) A dipole-dipole interaction between acetone molecules flipped in direction, but adjacent to each other in the same plane. (c) Demonstration of how quadrupole-quadrupole interactions are involved in the crystal lattice structure.
1151:
red phosphorus, the density goes to 2.2–2.4 g/cm and melting point to 590 °C, and when white phosphorus is transformed into the (also covalent) black phosphorus, the density becomes 2.69–3.8 g/cm and melting temperature ~200 °C. Both red and black phosphorus forms are significantly harder than white phosphorus.
505:
molecule, respectively. The δ- orienttowards the δ+ causing the acetone molecules to prefer to align in a few configurations in a δ- to δ+ orientation (pictured left). The dipole-dipole and other intermolecular interactions align to minimize energy in the solid state and determine the crystal lattice structure.
1191:), many molecular solids have directional intermolecular forces. This phenomenon can lead to anisotropic mechanical properties. Typically, a molecular solid is ductile when it has isotropic intermolecular interactions. This allows for dislocation between layers of the crystal much like metals. For example,
628:. For the second example, the δ- bromine atom in the diatomic bromine molecule is aligning with the less electronegative oxygen in the 1,4-dioxane. The oxygen in this case is viewed as δ+ compared to the bromine atom. This coordination results in a chain-like organization that stack into 2D and then 3D.
796:
of metals and ionic solids is ~ 1000 °C and greater, while molecular solids typically melt closer to 300 °C (see table), thus many corresponding substances are either liquid (ice) or gaseous (oxygen) at room temperature. This is due to the elements involved, the molecules they form, and the
450:
Van der Waals and London dispersion forces guide iodine to condense into a solid at room temperature. (a) A lewis dot structure of iodine and an analogous structure as a spacefill model. Purple balls represent iodine atoms. (b) Demonstration of how van der Waals and London dispersion forces guide the
1150:
Allotropes of phosphorus are useful to further demonstrate this structure-property relationship. White phosphorus, a molecular solid, has a relatively low density of 1.82 g/cm and melting point of 44.1 °C; it is a soft material which can be cut with a knife. When it is converted to the covalent
498:
The dipole-dipole interactions between the acetone molecules partially guide the organization of the crystal lattice structure. (a) A dipole-dipole interaction between acetone molecules stacked on top of one another. (b) A dipole-dipole interaction between acetone molecules in front and bock of each
647:
Coulombic interactions are manifested in some molecular solids. A well-studied example is the radical ion salt TTF-TCNQ with a conductivity of 5 x 10 Ω cm, much closer to copper (ρ = 6 x 10 Ω cm) than many molecular solids. The coulombic interaction in TTF-TCNQ stems from the large partial negative
641:
The partial ionic bonding between the TTF and TCNQ molecules partially guides the organization of the crystal structure. The van der Waals interactions of the core for TTF and TCNQ guide adjacent stacked columns. (a) A lewis dot structure and ball and stick model of TTF and TCNQ. The partial ionic
504:
For acetone dipole-dipole interactions are a major driving force behind the structure of its crystal lattice. The negative dipole is caused by oxygen. Oxygen is more electronegative than carbon and hydrogen, causing a partial negative (δ-) and positive charge (δ+) on the oxygen and remainder of the
550:
The hydrogen bonding between the acetic acid molecules partially guides the organization of the crystal lattice structure. (a) A lewis dot structure with the partial charges and hydrogen bond denoted with blue dashed line. A ball and stick model of acetic acid with hydrogen bond denoted with blue
683:
The structural transitions in phosphorus are reversible: upon releasing high pressure, black phosphorus gradually converts into the red phosphorus, and by vaporizing red phosphorus at 490 °C in an inert atmosphere and condensing the vapor, covalent red phosphorus can be transformed into the
1231:
The thermal properties of molecular solids (as, for instance, specific heat capacity, thermal expansion, and thermal conductance to name a few) are determined by the intra- and intermolecular vibrations of the atoms and molecules of the molecular solid. In molecular solids the transitions of an
599:
The halogen bonding between the bromine and 1,4-dioxane molecules partially guides the organization of the crystal lattice structure. (a) A lewis dot structure and ball and stick model of bromine and 1,4-dioxane. The halogen bond is between the bromine and 1,4-dioxane. (b) Demonstration of how
531:
resulting in a quadrupole. For naphthalene, this quadrupole manifests in a δ- and δ+ accumulating within and outside the ring system, respectively. Naphthalene assembles through the coordination of δ- of one molecules to the δ+ of another molecule. This results in 1D columns of naphthalene in a
513:
The quadrupole-quadrupole interactions between the naphthalene molecules partially guide the organization of the crystal lattice structure. (a) A lewis dot structure artificially colored to provide a qualitative map of where the partial charges exist for the quadrupole. A 3D representation of
783:
Since molecular solids are held together by relatively weak forces they tend to have low melting and boiling points, low mechanical strength, low electrical conductivity, and poor thermal conductivity.it will Also, depending on the structure of the molecule the intermolecular forces may have
494:
499:
other in the same plane. (c) A dipole-dipole interaction between acetone molecules flipped in direction, but adjacent to each other in the same plane. (d) Demonstration of how quadrupole-quadrupole interactions are involved in the crystal lattice structure.
472:. These characteristics make it unfavorable for argon to partake in metallic, covalent, and ionic bonds as well as most intermolecular interactions. It can though partake in van der Waals and London dispersion forces. These weak self-interactions are
536:
configuration. These columns then stack into 2D layers and then 3D bulk materials. Octafluoronaphthalene follows this path of organization to build bulk material except the δ- and δ+ are on the exterior and interior of the ring system, respectively.
1198:
One example of a ductile molecular solid, that can be bent 180°, is hexachlorobenzene (HCB). In this example the π-π interactions between the benzene cores are stronger than the halogen interactions of the chlorides. This difference leads to its
57:, respectively. Images of carbon dioxide (b) and caffeine (d) in the solid state at room temperature and atmosphere. The gaseous phase of the dry ice in image (b) is visible because the molecular solid is
2260:
Kistenmacher, T. J.; Phillips, T. E.; Cowan, D. O. (1974). "The
Crystal Structure of the 1:1 Radical Cation-Radical Anion Salt of 2,2'-bis-1,3-dithiole (TTF) and 7,7,8,8-tetracyanoquinodimethane (TCNQ)".
480:
packing when cooled below -189.3. Similarly iodine, a linear diatomic molecule has a net dipole of zero and can only partake in van der Waals interactions that are fairly isotropic. This results in the
676:
tetrahedra are no longer isolated, but connected by covalent bonds into polymer-like chains. Heating white phosphorus under high (GPa) pressures converts it to black phosphorus which has a layered,
519:
A quadrupole, like a dipole, is a permanent pole but the electric field of the molecule is not linear as in acetone, but in two dimensions. Examples of molecular solids with quadrupoles are
155:. These differences in the strength of force (i.e. covalent vs. van der Waals) and electronic characteristics (i.e. delocalized electrons) from other types of solids give rise to the unique
1223:
with ρ = 5 x 10 Ω cm but in such cases orbital overlap is evident in the crystal structure. Fullerenes, which are insulating, become conducting or even superconducting upon doping.
1996:
Allan, D. R.; Clark, S. J.; Ibberson, R. M.; Parsons, S.; Pulham, C. R.; Sawyer, L. (1999). "The
Influence of Pressure and Temperature on the Crystal Structure of Acetone".
1661:
Varughese, S.; Kiran, M. S. R. N.; Ramamurty, U.; Desiraju, G. R. (2013). "Nanoindentation in
Crystal Engineering: Quantifying Mechanical Properties of Molecular Crystals".
2695:
2351:
551:
dashed line. (b) Four acetic acid molecules in zig-zag hydrogen bonding in 1D. (c) Demonstration of how hydrogen bonding are involved in the crystal lattice structure.
240:
points compared to metal (iron), ionic (sodium chloride), and covalent solids (diamond). Examples of molecular solids with low melting and boiling temperatures include
178:
are semiconductors (ρ = 5 x 10 Ω cm). They are still substantially less than the conductivity of copper (ρ = 6 x 10 Ω cm). Molecular solids tend to have lower
2288:
Cohen, M. J.; Coleman, L. B.; Garito, A. F.; Heeger, A. J. (1974). "Electrical
Conductivity of Tetrathiofulvalinium Tetracyanoquinodimethane (TTF) (TCNQ)".
568:. For intermolecular hydrogen bonds the δ+ hydrogen interacts with a δ- on an adjacent molecule. Examples of molecular solids that hydrogen bond are water,
775:) units and are molecular solids at ambient conditions, but converted into covalent allotropes having atomic chains extending throughout the crystal.
642:
bond is between the cyano- and thio- motifs. (b) Demonstration of how van der Waals and partial ionic bonding guide the crystal lattice structure.
160:
587:
moiety (δ-) of the carboxylic on the adjacent molecule. This hydrogen bond leads a string of acetic acid molecules hydrogen bonding to minimize
1293:
Lehmann, C. W.; Stowasser, Frank (2007). "The
Crystal Structure of Anhydrous Beta-Caffeine as Determined from X-ray Powder-Diffraction Data".
2620:
2568:
2541:
2514:
2467:
2442:
2388:
2361:
2334:
437:). It is the lack or presence of other intermolecular interactions based on the atom or molecule that affords materials unique properties.
656:
One form of an element may be a molecular solid, but another form of that same element may not be a molecular solid. For example, solid
2593:
2226:
Reddy, C. M.; Krishan, G. R.; Ghosh, S. (2010). "Mechanical properties of molecular crystals—applications to crystal engineering".
2692:
520:
109:. Van der Waals, dipole interactions, quadrupole interactions, π–π interactions, hydrogen bonding, and halogen bonding (2–127
58:
2176:
Metrangolo, P.; Meyer, F.; Pilati, Tullio; Resnati, G.; Terraneo, G. (2008). "Halogen
Bonding in Supramolecular Chemistry".
613:
interaction with a less electronegative atom on an adjacent molecule. Examples of molecular solids that halogen bond are
2714:
1934:
Davey, R. J.; Schroeder, S. L.; Horst, J. H. T. (2013). "Nucleation of
Organic Crystals - A Molecular Perspective".
556:
A hydrogen bond is a specific dipole where a hydrogen atom has a partial positive charge (δ+) to due a neighboring
664:
called "white", "red", and "black" phosphorus. White phosphorus forms molecular crystals composed of tetrahedral P
433:
of the material is structured. All atoms and molecules can partake in van der Waals and London dispersion forces (
2642:
1176:
1172:
610:
1183:
structure of most molecules or the presence of functional groups capable of forming specific interactions (e.g.
133:
31:
2123:
187:
148:
102:
698:
156:
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till they reach the yield stress. Once the yield stress is reached, ductile solids undergo a period of
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and eventually fracture. Brittle solids fracture promptly after passing the yield stress. Due to the
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2297:
1898:
477:
171:
164:
144:
636:
594:
573:
533:
78:
1969:
Harris, Harris; Edward, M.; Blake, F. C. (1928). "The Atomic
Arrangement of Orthorhombic Iodine".
508:
2677:
2651:
2009:
576:
179:
2065:
Williams, J. H. (1993). "The
Molecular Electric QuadrupoleMoment and Solid-State Architecture".
493:
30:"Molecular crystal" redirects here. For a solid network of atoms covalently bound together, see
2404:
Simon, Arndt; Borrmann, Horst; Horakh, Jörg (1997). "On the
Polymorphism of White Phosphorus".
1232:
electron contribute negligibly to thermal properties compared to the vibrational contribution.
545:
2616:
2610:
2589:
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2537:
2531:
2510:
2463:
2438:
2432:
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2357:
2330:
2324:
2193:
1951:
1916:
1867:
1678:
1310:
1263:
Simon, A.; Peters, K. (1980). "Single-Crystal Refinement of the Structure of Carbon Dioxide".
1241:
1216:
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1122:
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992:
614:
588:
557:
524:
469:
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37:
2693:
https://www.boundless.com/chemistry/liquids-and-solids/types-of-crystals/molecular-crystals/
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2001:
1978:
1943:
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1859:
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to small molecules (i.e. naphthalene and water) to large molecules with tens of atoms (i.e.
129:
121:
106:
1911:
1886:
707:
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1192:
1015:
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465:
209:
2484:
2665:
2301:
1902:
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584:
482:
434:
125:
90:
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rings. The electronegativity of the atoms of this ring system and conjugation cause a
2708:
1184:
793:
261:
260:(see table below). The constituents of molecular solids range in size from condensed
233:
225:
137:
94:
2681:
2161:
2144:
2013:
564:. Hydrogen bonds are amongst the strong intermolecular interactions know other than
445:
1188:
528:
98:
2097:"Use of a CCD diffractometer in crystal structure determinations at high pressure"
17:
1164:
625:
249:
152:
113:
1215:
at 0.7 eV) is due to the weak intermolecular interactions, which result in low
2673:
2637:
2274:
2113:
2045:
2028:
1276:
721:
657:
591:. These strings of acetic acid molecules then stack together to build solids.
569:
461:
276:
Melting and boiling points of metallic, ionic, covalent, and molecular solids
86:
41:
Models of the packing of molecules in two molecular solids, carbon dioxide or
2417:
2309:
1212:
1211:
Molecular solids are generally insulators. This large band gap (compared to
1200:
1180:
1160:
661:
618:
457:
265:
2197:
2189:
1955:
1947:
1920:
1871:
1682:
1674:
1314:
1306:
429:. The intermolecular interactions between the constituents dictate how the
116:) are typically much weaker than the forces holding together other solids:
1850:
Desiraju, G. R. (2013). "Crystal Engineering: From Molecular to Crystal".
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1220:
952:
858:
832:
819:
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669:
473:
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257:
253:
175:
74:
54:
2078:
1982:
691:
1781:
Low Temperature Physics: The Crystal Structures of Argon and Its Alloys
1079:
1052:
1002:
935:
901:
871:
752:
622:
217:
183:
42:
1863:
1766:
The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals
2239:
2029:"X-Ray Powder Diffraction Investigation of Naphthalene up to 0.5 GPa"
2005:
1109:
1096:
1025:
965:
918:
884:
845:
760:
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molecules. Heating at ambient pressure to 250 °C or exposing to
606:
565:
269:
82:
50:
46:
2462:(in German) (91–100 ed.). Walter de Gruyter. pp. 675–681.
151:
such as the tetrathiafulvane-tetracyanoquinodimethane (TTF-TCNQ), a
635:
593:
544:
507:
492:
451:
organization of the crystal lattice from 1D to 3D (bulk material).
444:
245:
241:
197:
117:
110:
70:
36:
1219:. Some molecular solids exhibit electrical conductivity, such as
45:(a), and caffeine (c). The gray, red, and purple balls represent
2458:
Holleman, Arnold F; Wiberg, Egon; Wiberg, Nils (1985). "Arsen".
201:
1814:
Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity
1065:
194:
572:, and acetic acid. For acetic acid, the hydrogen (δ+) on the
147:, unlike metallic and certain covalent bonds. Exceptions are
784:
directionality leading to anisotropy of certain properties.
77:. The cohesive forces that bind the molecules together are
2095:
Dawson, A.; Allan, D. R.; Parsons, Simon; Ruf, M. (2004).
1768:. Cambridge, United Kingdom: Royal Society of Chemistry.
600:
halogen bonding can guide the crystal lattice structure.
476:
and result in the long-range ordering of the atoms into
2560:
Product engineering: molecular structure and properties
1746:
Haynes, W. M.; Lise, D. R.; Bruno, T. J., eds. (2016).
672:
converts white phosphorus to red phosphorus where the P
2353:
The Pearson Guide to Objective Chemistry for the AIEEE
2485:"Allotropes – Group 13, Group 14, Group 15, Group 16"
1834:
Organic Molecular Solids: Properties and Applications
1779:
Barret, C. S.; Meyer, L. (1965). Daunt, J. G. (ed.).
143:
Intermolecular interactions typically do not involve
797:weak intermolecular interactions of the molecules.
1885:Thakur, T. S.; Dubey, R.; Desiraju, G. R. (2015).
1575:. New York, New York: Oxford University Press Inc.
1195:are soft, resemble waxes and are easily deformed.
1171:stressed. Both ductile and brittle solids undergo
2124:20.500.11820/1ccaaabb-b17b-4282-a863-2675032f925f
729:White, red, violet, and black phosphorus samples
2329:. Jones & Bartlett Learning. p. 981.
421:Molecular solids may consist of single atoms,
2588:(86th ed.). Boca Raton (FL): CRC Press.
2380:Principles of descriptive inorganic chemistry
1593:. Hoboken, New Jersey: Wiley Eastern Limited.
8:
2530:Darrell D. Ebbing, Steven D. Gammon (2007).
1816:. Cambridge, UK: Cambridge University Press.
1627:. Cambridge, Massachusetts: Academic Press.
2323:John Olmsted, Gregory M. Williams (1997).
800:
605:A halogen bond is when an electronegative
2655:
2383:. University Science Books. p. 186.
2160:
2122:
2112:
2044:
1910:
489:Dipole-dipole and quadrupole interactions
2563:. Oxford University Press. p. 137.
2145:"The Structure of Bromine 1,4-Dioxanate"
1971:Journal of the American Chemical Society
1852:Journal of the American Chemical Society
802:Melting points of some molecular solids
686:
274:
2356:. Pearson Education India. p. 36.
2178:Angewandte Chemie International Edition
1936:Angewandte Chemie International Edition
1663:Angewandte Chemie International Edition
1252:
2255:
2253:
2251:
2249:
2221:
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2090:
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1912:10.1146/annurev-physchem-040214-121452
1845:
1843:
1827:
1825:
1823:
1807:
1805:
1798:. Oxford, UK: Oxford University Press.
1796:The Structures and Properties of Water
1759:
1757:
1741:
1739:
1737:
1735:
1733:
1731:
1729:
1727:
1656:
1654:
224:= 5 MPa m). Molecular solids have low
27:Solid consisting of discrete molecules
2586:CRC Handbook of Chemistry and Physics
1748:CRC Handbook of Chemistry and Physics
1725:
1723:
1721:
1719:
1717:
1715:
1713:
1711:
1709:
1707:
1700:. New York, New York: Academic Press.
1652:
1650:
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1384:
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1346:
1344:
1288:
1286:
1258:
1256:
523:. Naphthalene consists of two joined
521:octafluoronaphthalene and naphthalene
7:
1794:Eisenberg, D.; Kauzmann, W. (2005).
1584:
1582:
1550:
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1546:
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1342:
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1332:
1330:
1328:
1326:
1324:
1167:, or a combination depending on the
1891:Annual Review of Physical Chemistry
1463:Schwoerer, M.; Wolf, H. C. (2007).
1355:. Berlin, Germany: Springer-Verlag.
755:is a molecular solid composed of As
684:molecular solid, white phosphorus.
216:= 0.5 MPa m), and covalent solids (
2101:Journal of Applied Crystallography
1887:"Crystal Structure and Prediction"
1521:Patterson, J.; Bailey, B. (2010).
25:
2638:"Superconductivity in Fullerides"
2536:. Cengage Learning. p. 446.
2460:Lehrbuch der Anorganischen Chemie
1750:. Boca Raton, Florida: CRC Press.
1625:Intermolecular and Surface Forces
2615:. FK Publications. p. 550.
2437:. FK Publications. p. 548.
2326:Chemistry: the molecular science
2263:Acta Crystallographica Section B
2143:Hassel, O.; Hvoslef, J. (1954).
2033:Acta Crystallographica Section B
720:
713:
706:
697:
690:
105:, and in some molecular solids,
2509:. Academic Press. p. 524.
2162:10.3891/acta.chem.scand.08-0873
1783:. New York, New York: Springer.
1467:. Weinheim, Germany: Wiley-VCH.
1159:Molecular solids can be either
2027:Alt, H. C.; Kalus, J. (1982).
1493:Elementary Solid State Physics
583:hydrogen bonds with other the
1:
2067:Accounts of Chemical Research
1623:Israelachvili, J. N. (2011).
1353:Molecular Solid State Physics
1295:Chemistry: A European Journal
660:can crystallize as different
1525:. Berlin, Germany: Springer.
1405:. Berlin, Germany: Springer.
541:Hydrogen and halogen bonding
2609:AK Srivastava and PC Jain.
2431:AK Srivastava and PC Jain.
1764:O'Neil, M. J., ed. (2013).
1495:. London, England: Pearson.
2731:
1698:The Properties of Diamonds
1696:Field, J. E., ed. (1979).
788:Melting and boiling points
174:, although some, such as
170:Molecular solids are poor
83:dipole–dipole interactions
29:
2674:10.1103/RevModPhys.69.575
2643:Reviews of Modern Physics
2584:Lide, D. R., ed. (2005).
2275:10.1107/s0567740874003669
2149:Acta Chemica Scandinavica
2114:10.1107/s0021889804007149
2046:10.1107/s056774088200942x
1591:Principles of Solid State
1277:10.1107/s0567740880009879
417:Composition and structure
149:charge-transfer complexes
2418:10.1002/cber.19971300911
2310:10.1103/PhysRevB.10.1298
1836:. Boca Raton: CRC Press.
1465:Organic Molecular Solids
103:London dispersion forces
32:Network covalent bonding
2612:Chemistry Vol (1 and 2)
2505:James E. House (2008).
2434:Chemistry Vol (1 and 2)
2377:Gary Wulfsberg (1991).
1998:Chemical Communications
1832:Jones, W., ed. (1997).
1401:Fahlman, B. D. (2011).
1217:charge carrier mobility
566:ion-dipole interactions
132:, 700–900 kJ mol), and
87:quadrupole interactions
73:consisting of discrete
2636:O. Gunnarsson (1997).
2190:10.1002/anie.200800128
1948:10.1002/anie.201204824
1812:Harvey, G. R. (1991).
1675:10.1002/anie.201205002
1307:10.1002/chem.200600973
644:
632:Coulombic interactions
602:
553:
516:
501:
453:
107:coulombic interactions
62:
2487:. Chemistry Explained
2350:Singhal Atul (2009).
1573:The Physics of Solids
1351:Hall, George (1965).
1207:Electrical properties
1155:Mechanical properties
759:units. Some forms of
745:and black phosphorus
639:
597:
548:
511:
496:
448:
172:electrical conductors
167:of molecular solids.
145:delocalized electrons
40:
2483:Masters, Anthony F.
1589:Keer, H. V. (1993).
1491:Omar, M. A. (2002).
734:of white phosphorus
483:bipyramidal symmetry
441:Van der Waals forces
427:polyatomic molecules
208:= 50 MPa m), ionic (
79:van der Waals forces
2666:1997RvMP...69..575G
2507:Inorganic chemistry
2302:1974PhRvB..10.1298C
2079:10.1021/ar00035a005
1983:10.1021/ja01393a009
1903:2015ARPC...66...21T
1571:Turton, R. (2010).
1523:Solid-State Physics
1403:Materials Chemistry
1265:Acta Crystallogr. B
1177:plastic deformation
1173:elastic deformation
803:
792:The characteristic
478:face centered cubic
277:
140:, 150–900 kJ mol).
124:, 400–500 kJ mol),
2715:Chemical compounds
2698:2014-01-03 at the
2557:James Wei (2007).
2406:Chemische Berichte
1227:Thermal properties
801:
751:Similarly, yellow
739:Structures of red
645:
609:participates in a
603:
554:
517:
502:
454:
275:
180:fracture toughness
165:thermal properties
63:
2622:978-81-88597-83-3
2570:978-0-19-515917-2
2543:978-0-618-85748-7
2533:General Chemistry
2516:978-0-12-356786-4
2469:978-3-11-007511-3
2444:978-81-88597-83-3
2390:978-0-935702-66-8
2363:978-81-317-1359-4
2336:978-0-8151-8450-8
2290:Physical Review B
2184:(33): 6114–6127.
2039:(10): 2595–2600.
1864:10.1021/ja403264c
1858:(27): 9952–9967.
1669:(10): 2701–2712.
1301:(10): 2908–2911.
1271:(11): 2750–2751.
1242:Bonding in solids
1138:
1137:
767:are composed of S
749:
748:
680:-like structure.
643:
615:hexachlorobenzene
601:
552:
515:
500:
452:
414:
413:
18:Molecular crystal
16:(Redirected from
2722:
2686:
2685:
2659:
2657:cond-mat/9611150
2633:
2627:
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2606:
2600:
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2401:
2395:
2394:
2374:
2368:
2367:
2347:
2341:
2340:
2320:
2314:
2313:
2296:(4): 1298–1307.
2285:
2279:
2278:
2257:
2244:
2243:
2240:10.1039/c003466e
2234:(8): 2296–2314.
2223:
2202:
2201:
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2167:
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2140:
2129:
2128:
2126:
2116:
2092:
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2048:
2024:
2018:
2017:
2006:10.1039/A900558G
1993:
1987:
1986:
1977:(6): 1583–1600.
1966:
1960:
1959:
1942:(8): 2166–2179.
1931:
1925:
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1281:
1280:
1260:
1193:plastic crystals
804:
724:
717:
710:
701:
694:
687:
640:
598:
562:functional group
549:
512:
497:
449:
320:Sodium chloride
278:
153:radical ion salt
130:Coulomb’s forces
122:metallic bonding
95:hydrogen bonding
91:π–π interactions
21:
2730:
2729:
2725:
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2700:Wayback Machine
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2073:(11): 593–598.
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1990:
1968:
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813:
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733:
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654:
634:
581:carboxylic acid
558:electronegative
543:
491:
443:
431:crystal lattice
419:
297:
290:
262:monatomic gases
237:
229:
223:
215:
210:sodium chloride
207:
191:
99:halogen bonding
67:molecular solid
35:
28:
23:
22:
15:
12:
11:
5:
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2396:
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2342:
2335:
2315:
2280:
2269:(3): 763–768.
2245:
2203:
2168:
2130:
2107:(3): 410–416.
2084:
2052:
2019:
2000:(8): 751–752.
1988:
1961:
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1234:
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1205:
1185:hydrogen bonds
1156:
1153:
1147:
1146:
1144:higher alkanes
1136:
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1119:
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281:Type of Solid
235:
227:
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213:
205:
200:) than metal (
189:
138:covalent bonds
134:network solids
26:
24:
14:
13:
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3:
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1976:
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1962:
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1226:
1224:
1222:
1218:
1214:
1206:
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1202:
1196:
1194:
1190:
1189:halogen bonds
1186:
1182:
1178:
1174:
1170:
1166:
1162:
1154:
1152:
1145:
1140:
1139:
1133:
1131:
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1120:
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917:
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878:
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869:
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856:
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850:
844:
843:
839:
837:
831:
830:
826:
824:
818:
817:
809:
806:
805:
798:
795:
794:melting point
787:
785:
778:
776:
766:
762:
754:
744:
741:
738:
736:
731:
728:
727:
723:
719:
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703:
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638:
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522:
510:
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447:
440:
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409:
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389:
386:
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367:
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96:
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88:
84:
80:
76:
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68:
60:
56:
52:
48:
44:
39:
33:
19:
2647:
2641:
2631:
2611:
2604:
2585:
2579:
2559:
2552:
2532:
2525:
2506:
2500:
2489:. Retrieved
2478:
2459:
2453:
2433:
2426:
2409:
2405:
2399:
2379:
2372:
2352:
2345:
2325:
2318:
2293:
2289:
2283:
2266:
2262:
2231:
2228:CrystEngComm
2227:
2181:
2177:
2171:
2152:
2148:
2104:
2100:
2070:
2066:
2036:
2032:
2022:
1997:
1991:
1974:
1970:
1964:
1939:
1935:
1929:
1894:
1890:
1880:
1855:
1851:
1833:
1813:
1795:
1789:
1780:
1774:
1765:
1747:
1697:
1691:
1666:
1662:
1624:
1590:
1572:
1522:
1492:
1464:
1402:
1352:
1298:
1294:
1268:
1264:
1230:
1210:
1197:
1169:crystal face
1158:
1149:
791:
782:
750:
682:
655:
646:
604:
555:
529:ring current
518:
503:
456:Argon, is a
455:
420:
376:Naphthalene
169:
142:
66:
64:
2412:(9): 1235.
1201:flexibility
626:1,4-dioxane
611:noncovalent
589:free energy
570:amino acids
534:herringbone
460:that has a
250:naphthalene
2650:(2): 575.
2491:2009-01-06
1248:References
1181:asymmetric
779:Properties
662:allotropes
658:phosphorus
652:Allotropes
525:conjugated
462:full octet
401:Molecular
387:Molecular
373:Molecular
359:Molecular
345:Molecular
234:boiling (T
226:melting (T
161:electronic
157:mechanical
1897:: 21–42.
1213:germanium
1141:See also
619:cocrystal
474:isotropic
468:, and is
458:noble gas
425:, and/or
404:Caffeine
390:Nicotine
331:Covalent
303:Metallic
284:Material
266:fullerene
75:molecules
59:subliming
2709:Category
2696:Archived
2682:18025631
2198:18651626
2014:54901610
1956:23307268
1921:25422850
1872:23750552
1683:23315913
1315:17200930
1236:See also
1221:TTF-TCNQ
765:selenium
678:graphite
670:sunlight
585:carbonyl
560:atom or
470:nonpolar
423:diatomic
334:Diamond
272:atoms).
268:with 60
258:caffeine
254:nicotine
176:TTF-TCNQ
118:metallic
55:nitrogen
2662:Bibcode
2298:Bibcode
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1899:Bibcode
1165:brittle
1161:ductile
960:−101.6
947:−129.8
930:−138.3
913:−165.0
896:−181.8
879:−182.4
866:−210.0
853:−218.8
840:−219.6
827:−259.1
807:Formula
753:arsenic
742:violet
623:bromine
579:of the
574:alcohol
435:sterics
354:-185.9
351:-189.3
218:diamond
193:= 0.08
184:sucrose
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1117:119.0
1104:113.7
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1037:−29.7
1020:−50.8
1010:−80.0
997:−80.0
987:−86.8
977:−95.3
771:(or Se
761:sulfur
617:and a
607:halide
577:moiety
466:charge
410:519.9
407:235.6
382:217.9
362:Water
348:Argon
337:4,440
326:1,465
317:Ionic
312:2,861
309:1,538
270:carbon
256:, and
163:, and
53:, and
51:oxygen
47:carbon
2678:S2CID
2652:arXiv
2010:S2CID
1060:−7.2
464:, no
379:80.1
306:Iron
298:(°C)
291:(°C)
246:water
242:argon
126:ionic
71:solid
69:is a
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2590:ISBN
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2385:ISBN
2358:ISBN
2331:ISBN
2194:PMID
1952:PMID
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202:iron
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2306:doi
2271:doi
2236:doi
2186:doi
2157:doi
2119:hdl
2109:doi
2075:doi
2041:doi
2002:doi
1979:doi
1944:doi
1907:doi
1860:doi
1856:135
1671:doi
1303:doi
1273:doi
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