47:
429:
259:
1012:
38:
668:
663:
789:
950:, with one of the first observed instances reported in carboxypeptidase A. Inhibition of the enzyme occurs by removal and chelation of the metal ion required for catalytic activity, leaving an inactive apoenzyme. 1,10-Phenanthroline targets mainly zinc metallopeptidases, with a much lower affinity for calcium.
958:
A variety of substituted derivatives of phen have been examined as ligands. Substituents at the 2,9 positions confer protection for the attached metal, inhibiting the binding of multiple equivalents of the phenanthroline. Such bulky ligands also favor trigonal or tetrahedral coordination at the
1147:
Alkyllithium reagents form deeply colored derivatives with phenanthroline. The alkyllithium content of solutions can be determined by treatment of such reagents with small amounts of phenanthroline (ca. 1 mg) followed by titration with alcohols to a colourless
2034:
Kohler, Lars; Hayes, Dugan; Hong, Jiyun; Carter, Tyler J.; Shelby, Megan L.; Fransted, Kelly A.; Chen, Lin X.; Mulfort, Karen L. (2016). "Synthesis, structure, ultrafast kinetics, and light-induced dynamics of CuHETPHEN chromophores".
676:
643:
912:(bipy) with the advantage that the two nitrogen donors are preorganized for chelation. Phenanthroline is a stronger base than bipy. According to one ligand ranking scale, phen is a weaker donor than bipy.
1782:
Leipoldt, J.G.; Lamprecht, G.J.; Steynberg, E.C. (1991). "Kinetics of the substitution of acetylacetone in acetylactonato-1,5-cyclooctadienerhodium(I) by derivatives of 1,10-phenantrholine and 2,2
1422:
Bellér, G. B.; Lente, G. B.; Fábián, I. N. (2010). "Central Role of
Phenanthroline Mono-N-oxide in the Decomposition Reactions of Tris(1,10-phenanthroline)iron(II) and -iron(III) Complexes".
931:+1.06 V. The reduced ferrous form has a deep red colour and the oxidised form is light-blue. The pink complex has been resolved into its Δ and Λ isomers. The complex is bioactive.
1660:
Accorsi, Gianluca; Listorti, Andrea; Yoosaf, K.; Armaroli, Nicola (2009). "1,10-Phenanthrolines: Versatile building blocks for luminescent molecules, materials and metal complexes".
802:
835:. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called
478:
1305:
Halcrow, Barbara E.; Kermack, William O. (1946). "43. Attempts to find new antimalarials. Part XXIV. Derivatives of o-phenanthroline (7 : 8 : 3
1346:
Teng, Qiaoqiao; Huynh, Han Vinh (2017). "A Unified Ligand
Electronic Parameter Based on C NMR Spectroscopy of N-Heterocyclic Carbene Complexes".
1011:
2018:
1981:
1948:
1915:
1882:
1644:
1474:
1265:
1245:
1232:
1205:
1600:
Felber, Jean-Pierre; Coombs, Thomas L.; Vallee, Bert L. (1962). "The mechanism of inhibition of carboxypeptidase A by 1,10-phenanthroline".
128:
46:
1573:
Pallenberg A. J.; Koenig K. S.; Barnhart D. M. (1995). "Synthesis and
Characterization of Some Copper(I) Phenanthroline Complexes".
443:
1543:
Armaroli N (2001). "Photoactive Mono- and
Polynuclear Cu(I)-Phenanthrolines. A Viable Alternative to Ru(Ii)-Polypyridines?".
624:
809:
726:
708:
368:
1260:
Luman, C.R. and
Castellano, F.N. (2003) "Phenanthroline Ligands" in Comprehensive Coordination Chemistry II. Elsevier.
667:
407:
2098:
Lin, Ho-Shen; Paquette, Leo A. (1994). "A Convenient Method for
Determining the Concentration of Grignard Reagents".
1189:
600:
1490:
Dwyer, F. P.; Gyarfas, Eleonora C.; Rogers, W. P.; Koch, Judith H. (1952). "Biological
Activity of Complex Ions".
2135:
2130:
1635:
Salvesen, GS & Nagase, H (2001). "Inhibition of proteolytic enzymes". In Beynon, Rob & Bond, J S (eds.).
266:
1700:"Ni(I)–Alkyl Complexes Bearing Phenanthroline Ligands: Experimental Evidence for CO2 Insertion at Ni(I) Centers"
2140:
1698:
Somerville, Rosie J.; Odena, Carlota; Obst, Marc F.; Hazari, Nilay; Hopmann, Kathrin H.; Martin, Ruben (2020).
37:
1457:
George B. Kauffman; Lloyd T. Takahashi (1966). "Resolution of the tris-(1,10-Phenanthroline)Nickel(II) Ion".
254:
847:
188:
180:
690:
662:
655:
120:
1711:
1501:
1149:
59:
700:
1186:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
718:
424:
77:
1525:
1404:
928:
867:
140:
909:
763:
2076:
2052:
2014:
1977:
1944:
1911:
1878:
1847:
1737:
1677:
1640:
1617:
1517:
1470:
1439:
1363:
1328:
1261:
1241:
1201:
1153:
920:
915:
Several homoleptic complexes are known of the type . Particularly well studied is , called "
2107:
2044:
2006:
1969:
1936:
1903:
1870:
1837:
1829:
1795:
1764:
1727:
1719:
1669:
1609:
1582:
1552:
1509:
1492:
1462:
1431:
1394:
1355:
1320:
1287:
1193:
947:
943:
878:
832:
578:
506:
730:
385:
377:
216:
924:
859:
288:
208:
95:
1964:
Zhu, Lingui; Altman, Ryan A. (2013). "3,4,7,8-Tetramethyl-1,10-phenanthroline (Tmphen)".
1715:
1505:
428:
258:
160:
87:
1931:
Vallée, Frédéric; Kühn, Fritz E.; Korinth, Valentina A. (2013). "Bathophenanthroline".
1842:
1817:
1732:
1699:
780:
1278:
Sammes, Peter G.; Yahioglu, Gokhan (1994). "1,10-Phenanthroline: A versatile ligand".
850:, forming strong complexes with most metal ions. It is often sold as the monohydrate.
2124:
1799:
1315:
1059:
968:
874:
567:
557:
247:
1940:
1408:
746:
1529:
885:
881:
836:
829:
771:
714:
341:
1755:
Preston, H. S.; Kennard, C. H. L. (1969). "Crystal
Structure of di-mu-Chloro-sym-
722:
333:
2071:
1197:
1046:
964:
2010:
1973:
1907:
1874:
1466:
2111:
1818:"Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides"
589:
529:
199:
17:
1759:-Dichloro-Bis-(2,9-Dimethyl-1,10-Phenanthroline)dinickel(II)-2-Chloroform".
1399:
1382:
1237:
396:
2056:
1851:
1741:
1681:
1621:
1521:
1443:
1367:
1332:
1833:
1768:
1723:
1639:. Vol. 1 (2nd ed.). Oxford University Press. pp. 105–130.
1324:
1291:
893:
889:
863:
227:
1613:
1586:
236:
2048:
1359:
1165:
916:
767:
547:
320:
267:
1435:
908:
In terms of its coordination properties, phenanthroline is similar to
1673:
1556:
1513:
843:
171:
779:
Except where otherwise noted, data are given for materials in their
308:
1816:
Rezazadeh, Sina; Devannah, Vijayarajan; Watson, Donald A. (2017).
963:
when treated with metal dihalides (M = Fe, Co, Ni). By contrast,
897:
696:
352:
151:
127:
119:
109:
738:
1019:
742:
299:
452:
InChI=1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
1997:
Altman, Ryan A. (2008). "1,10-Phenanthroline, 4,7-Dimethoxy".
462:
InChI=1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
734:
412:
638:
mild neurotoxin, strong nephrotoxin, and powerful diuretic
1383:"Application of chelate Compounds in Analytical Chemistry"
979:
Basicities of 1,10-Phenanthrolines and 2,2'-Bipyridine
797:
1898:Liu, Guosheng; Wu, Yichen (2012). "Bathocuproine".
491:
monohydrate: C1=CC2=C(C3=C(C=CC=N3)C=C2)N=C1.O
959:metal. Phen itself form complexes of the type Cl
858:Phenanthroline may be prepared by two successive
340:
332:
562:118.56 °C (245.41 °F; 391.71 K)
94:
86:
1999:Encyclopedia of Reagents for Organic Synthesis
1966:Encyclopedia of Reagents for Organic Synthesis
1933:Encyclopedia of Reagents for Organic Synthesis
1900:Encyclopedia of Reagents for Organic Synthesis
1867:Encyclopedia of Reagents for Organic Synthesis
1568:
1566:
1168: – Complex of Fe by ortho-phenanthroline
8:
2070:Fagan, Paul J.; Nugent, William A. (1998).
1010:
923:determination of Fe(II). It is used as a
427:
257:
215:
207:
29:
1841:
1811:
1809:
1731:
1637:Proteolytic Enzymes: A Practical Approach
1398:
1143:As an indicator for alkyllithium reagents
384:
376:
1822:Journal of the American Chemical Society
1704:Journal of the American Chemical Society
1693:
1691:
977:
934:Copper(I) forms , which is luminescent.
877:, and an oxidizing agent, traditionally
2072:"1-Phenyl-2,3,4,5-Tetramethylphosphole"
1177:
1053:2,9-Dimethyl-4,7-diphenylphenanthroline
483:
448:
423:
235:
1865:Nilsson, Peter (2012). "Neocuproine".
248:
1233:CRC Handbook of Chemistry and Physics
1225:
1223:
1221:
1219:
1217:
455:Key: DGEZNRSVGBDHLK-UHFFFAOYSA-N
187:
179:
159:
7:
842:Abbreviated "phen", it is used as a
1788:Journal of Organometallic Chemistry
465:Key: DGEZNRSVGBDHLK-UHFFFAOYAW
323:
307:
25:
1461:. Vol. 5. pp. 227–232.
1115:4,7-dimethoxy-1,10-phenanthroline
1100:3,4,7,8-tetramethylphenanthroline
1230:Haynes, William M., ed. (2016).
1085:5,6-dimethyl-1,10-phenanthroline
1074:4,7-diphenyl-1,10-phenanthroline
1066:4,7-dimethyl-1,10-phenanthroline
1040:2,9-dimethyl-1,10-phenanthroline
787:
666:
661:
45:
36:
1941:10.1002/047084289X.rn01319.pub2
783:(at 25 °C , 100 kPa).
1190:The Royal Society of Chemistry
625:Occupational safety and health
1:
27:Heterocyclic organic compound
1800:10.1016/0022-328X(91)83069-G
1198:10.1039/9781849733069-FP001
1156:may be similarly titrated.
1130:2,6-dimesitylphenanthroline
1032:5-nitro-1,10-phenanthroline
971:form 1:1 complexes such as
900:followed by a cyclization.
279:monohydrate: 627-114-9
2157:
2086:, vol. 9, p. 653
2011:10.1002/047084289X.rn00918
1974:10.1002/047084289X.rn01515
1908:10.1002/047084289X.rn01392
1875:10.1002/047084289X.rn01440
1467:10.1002/9780470132395.ch60
1387:Pure and Applied Chemistry
1009:
942:1,10-Phenanthroline is an
919:." It can be used for the
534:180.21 g/mol
2112:10.1080/00397919408010560
896:which condenses with the
777:
752:
642:
622:
617:
499:
474:
439:
70:
58:
53:
44:
35:
1662:Chemical Society Reviews
1545:Chemical Society Reviews
1280:Chemical Society Reviews
709:Precautionary statements
1400:10.1351/pac197334010013
938:Bioinorganic chemistry
904:Coordination chemistry
848:coordination chemistry
1192:. 2014. p. 211.
1834:10.1021/jacs.7b04312
1769:10.1039/J19690002682
1724:10.1021/jacs.0c04695
1325:10.1039/jr9460000155
1313:-pyridoquinoline)".
1292:10.1039/cs9942300327
1080:bathophenanthroline
954:Related phen ligands
542:colourless crystals
486:c1cc2ccc3cccnc3c2nc1
60:Preferred IUPAC name
2037:Dalton Transactions
1716:2020JAChS.14210936S
1710:(25): 10936–10941.
1614:10.1021/bi00908a006
1587:10.1021/ic00115a009
1575:Inorganic Chemistry
1506:1952Natur.170..190D
1459:Inorganic Syntheses
1424:Inorganic Chemistry
1348:Dalton Transactions
1001:1,10-phenanthroline
980:
822:1,10-Phenanthroline
579:Solubility in water
141:Beilstein Reference
99: (monohydrate)
64:1,10-Phenanthroline
32:
2049:10.1039/c6dt00324a
1381:Belcher R (1973).
1360:10.1039/C6DT04222H
993:comment/alt. name
978:
929:standard potential
888:. Dehydration of
810:Infobox references
753:Related compounds
592:in other solvents
383:monohydrate:
339:monohydrate:
214:monohydrate:
186:monohydrate:
126:monohydrate:
93:monohydrate:
30:
2106:(17): 2503–2506.
2084:Collected Volumes
2077:Organic Syntheses
2043:(24): 9871–9883.
2020:978-0-471-93623-7
1983:978-0-471-93623-7
1950:978-0-471-93623-7
1917:978-0-471-93623-7
1884:978-0-471-93623-7
1828:(24): 8110–8113.
1646:978-0-19-963662-4
1581:(11): 2833–2840.
1500:(4318): 190–191.
1476:978-0-470-13239-5
1436:10.1021/ic902554b
1266:978-0-08-043748-4
1247:978-1-4987-5429-3
1240:. p. 3.444.
1236:(97th ed.).
1207:978-0-85404-182-4
1154:Grignard reagents
1140:
1139:
996:numbering scheme
948:metallopeptidases
871:-phenylenediamine
818:Chemical compound
816:
815:
759:Related compounds
691:Hazard statements
595:acetone, ethanol
408:CompTox Dashboard
129:Interactive image
121:Interactive image
16:(Redirected from
2148:
2136:Chelating agents
2131:Redox indicators
2116:
2115:
2095:
2089:
2087:
2080:
2067:
2061:
2060:
2031:
2025:
2024:
1994:
1988:
1987:
1961:
1955:
1954:
1928:
1922:
1921:
1895:
1889:
1888:
1862:
1856:
1855:
1845:
1813:
1804:
1803:
1785:
1779:
1773:
1772:
1752:
1746:
1745:
1735:
1695:
1686:
1685:
1674:10.1039/B806408N
1668:(6): 1690–2300.
1657:
1651:
1650:
1632:
1626:
1625:
1597:
1591:
1590:
1570:
1561:
1560:
1557:10.1039/b000703j
1540:
1534:
1533:
1514:10.1038/170190a0
1487:
1481:
1480:
1454:
1448:
1447:
1430:(9): 3968–3970.
1419:
1413:
1412:
1402:
1378:
1372:
1371:
1343:
1337:
1336:
1312:
1308:
1302:
1296:
1295:
1275:
1269:
1258:
1252:
1251:
1227:
1212:
1211:
1182:
1014:
984:phen derivative
981:
860:Skraup reactions
833:organic compound
800:
794:
791:
790:
748:
744:
740:
736:
732:
728:
724:
720:
716:
702:
698:
670:
665:
507:Chemical formula
432:
431:
416:
414:
388:
380:
344:
336:
325:
311:
289:Gmelin Reference
269:
261:
250:
239:
219:
211:
191:
183:
163:
131:
123:
98:
90:
49:
40:
33:
21:
2156:
2155:
2151:
2150:
2149:
2147:
2146:
2145:
2141:Phenanthrolines
2121:
2120:
2119:
2097:
2096:
2092:
2082:
2069:
2068:
2064:
2033:
2032:
2028:
2021:
1996:
1995:
1991:
1984:
1963:
1962:
1958:
1951:
1930:
1929:
1925:
1918:
1897:
1896:
1892:
1885:
1864:
1863:
1859:
1815:
1814:
1807:
1783:
1781:
1780:
1776:
1761:J. Chem. Soc. A
1754:
1753:
1749:
1697:
1696:
1689:
1659:
1658:
1654:
1647:
1634:
1633:
1629:
1599:
1598:
1594:
1572:
1571:
1564:
1542:
1541:
1537:
1489:
1488:
1484:
1477:
1456:
1455:
1451:
1421:
1420:
1416:
1380:
1379:
1375:
1345:
1344:
1340:
1310:
1306:
1304:
1303:
1299:
1277:
1276:
1272:
1259:
1255:
1248:
1229:
1228:
1215:
1208:
1184:
1183:
1179:
1175:
1162:
1145:
1124:
1109:
1094:
1020:2,2'-bipyridine
990:
974:
962:
956:
940:
925:redox indicator
910:2,2'-bipyridine
906:
873:, catalyzed by
856:
819:
812:
807:
806:
805: ?)
796:
792:
788:
784:
770:
766:
764:2,2'-bipyridine
760:
711:
693:
679:
658:
635:
609:
581:
523:
519:
515:
509:
495:
492:
487:
482:
481:
470:
467:
466:
463:
457:
456:
453:
447:
446:
435:
417:
410:
391:
363:
347:
326:
314:
291:
282:
242:
222:
194:
166:
143:
134:
113:
102:
80:
66:
65:
31:Phenanthroline
28:
23:
22:
15:
12:
11:
5:
2154:
2152:
2144:
2143:
2138:
2133:
2123:
2122:
2118:
2117:
2090:
2062:
2026:
2019:
1989:
1982:
1956:
1949:
1923:
1916:
1890:
1883:
1857:
1805:
1794:(2): 259–263.
1774:
1747:
1687:
1652:
1645:
1627:
1608:(2): 231–238.
1592:
1562:
1551:(2): 113–124.
1535:
1482:
1475:
1449:
1414:
1373:
1354:(3): 614–627.
1338:
1297:
1270:
1253:
1246:
1213:
1206:
1176:
1174:
1171:
1170:
1169:
1161:
1158:
1144:
1141:
1138:
1137:
1134:
1131:
1127:
1126:
1122:
1119:
1116:
1112:
1111:
1107:
1104:
1101:
1097:
1096:
1092:
1089:
1086:
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1081:
1078:
1075:
1071:
1070:
1067:
1063:
1062:
1057:
1054:
1050:
1049:
1044:
1041:
1037:
1036:
1033:
1029:
1028:
1025:
1022:
1016:
1015:
1008:
1005:
1002:
998:
997:
994:
991:
988:
985:
972:
960:
955:
952:
939:
936:
905:
902:
855:
852:
817:
814:
813:
808:
786:
785:
781:standard state
778:
775:
774:
761:
758:
755:
754:
750:
749:
712:
707:
704:
703:
694:
689:
686:
685:
680:
675:
672:
671:
659:
654:
651:
650:
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636:
633:
630:
629:
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619:
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614:
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582:
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570:
564:
563:
560:
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536:
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501:
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477:
476:
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471:
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450:
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441:
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365:
364:
362:
361:
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349:
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337:
329:
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313:
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304:
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296:
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271:
263:
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196:
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148:
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139:
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124:
116:
114:
107:
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103:
101:
100:
91:
83:
81:
76:
73:
72:
68:
67:
63:
62:
56:
55:
51:
50:
42:
41:
26:
24:
18:Phenanthroline
14:
13:
10:
9:
6:
4:
3:
2:
2153:
2142:
2139:
2137:
2134:
2132:
2129:
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2126:
2113:
2109:
2105:
2101:
2100:Synth. Commun
2094:
2091:
2085:
2079:
2078:
2073:
2066:
2063:
2058:
2054:
2050:
2046:
2042:
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2027:
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2016:
2012:
2008:
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1993:
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1927:
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1831:
1827:
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1812:
1810:
1806:
1801:
1797:
1793:
1789:
1786:-dipyridyl".
1778:
1775:
1770:
1766:
1763:: 2682–2685.
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1758:
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1743:
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1316:J. Chem. Soc.
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1087:
1084:
1083:
1079:
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1068:
1065:
1064:
1061:
1060:Bathocuproine
1058:
1055:
1052:
1051:
1048:
1045:
1042:
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1038:
1034:
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1030:
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969:bathocuproine
966:
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926:
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875:sulfuric acid
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613:4.84 (phenH)
612:
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249:ECHA InfoCard
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189:ChEMBL1255788
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52:
48:
43:
39:
34:
19:
2103:
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2040:
2036:
2029:
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1998:
1992:
1965:
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1932:
1926:
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1602:Biochemistry
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1595:
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1256:
1231:
1185:
1180:
1146:
957:
941:
933:
914:
907:
886:nitrobenzene
882:arsenic acid
868:
857:
841:
837:phenanthrene
830:heterocyclic
825:
821:
820:
772:phenanthrene
682:
644:
634:Main hazards
623:
604:
353:RTECS number
181:ChEMBL415879
71:Identifiers
1319:: 155–157.
1047:neocuproine
965:neocuproine
921:photometric
677:Signal word
628:(OHS/OSH):
539:Appearance
500:Properties
255:100.000.572
161:CHEBI:44975
2125:Categories
1286:(5): 327.
1173:References
1106:3,4,7,8-Me
656:Pictograms
590:Solubility
552:1.31 g/cm
530:Molar mass
386:KSX215X00E
378:W4X6ZO7939
200:ChemSpider
108:3D model (
78:CAS Number
1393:: 13–27.
1309: : 2
1238:CRC Press
1121:4,7-(MeO)
944:inhibitor
854:Synthesis
727:P301+P310
647:labelling
397:UN number
360:SF8300000
276:200-629-2
268:EC Number
96:5144-89-8
2057:26924711
1852:28594543
1742:32520556
1682:19587962
1622:13892106
1522:12982853
1444:20415494
1409:44054260
1368:27924321
1333:20983293
1160:See also
1150:endpoint
1136:HETPHEN
894:acrolein
890:glycerol
864:glycerol
618:Hazards
228:DrugBank
1843:5531607
1733:7351122
1712:Bibcode
1530:6483735
1502:Bibcode
1166:Ferroin
1133:unknown
1077:unknown
1056:unknown
1043:unknown
917:ferroin
879:aqueous
828:) is a
803:what is
801: (
768:ferroin
601:Acidity
548:Density
524:
321:PubChem
237:DB02365
146:126461
88:66-71-7
2055:
2017:
1980:
1947:
1914:
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1493:Nature
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1091:5,6-Me
892:gives
844:ligand
798:verify
795:
683:Danger
572:409.2
479:SMILES
309:C00604
172:ChEMBL
54:Names
2003:eEROS
1757:trans
1526:S2CID
1405:S2CID
1125:phen
1110:phen
1095:phen
1069:5.97
1035:3.57
1027:bipy
927:with
898:amine
866:with
584:high
444:InChI
401:2811
342:21226
294:4040
217:19955
152:ChEBI
110:JSmol
2053:PMID
2015:ISBN
1978:ISBN
1945:ISBN
1912:ISBN
1879:ISBN
1848:PMID
1738:PMID
1678:PMID
1641:ISBN
1618:PMID
1518:PMID
1471:ISBN
1440:PMID
1364:PMID
1329:PMID
1262:ISBN
1242:ISBN
1202:ISBN
1118:6.45
1103:6.31
1088:5.20
1024:4.30
1007:phen
1004:4.86
967:and
826:phen
747:P501
743:P405
739:P391
735:P330
731:P321
723:P273
719:P270
715:P264
701:H410
697:H301
369:UNII
334:1318
300:KEGG
209:1278
2108:doi
2045:doi
2007:doi
1970:doi
1937:doi
1904:doi
1871:doi
1838:PMC
1830:doi
1826:139
1796:doi
1792:402
1765:doi
1728:PMC
1720:doi
1708:142
1670:doi
1610:doi
1583:doi
1553:doi
1510:doi
1498:170
1463:doi
1432:doi
1395:doi
1356:doi
1321:doi
1288:doi
1194:doi
946:of
884:or
862:of
846:in
645:GHS
413:EPA
324:CID
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