STERIC INTERACTIONS IN 2-SUBSTITUTED IMIDAZOLES - THE MOLECULAR-STRUCTURE OF 1-METHYL-2-PHENYLIMIDAZOLE AND 1-METHYL-4-PHENYLIMIDAZOLE

被引：9

作者：

HALLOWS, WA

CARPENTER, GB

PEVEAR, KA

SWEIGART, DA

机构：

[1] Department of Chemistry, Brown University, Providence, Rhode Island

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 04期

关键词：

D O I：

10.1002/jhet.5570310435

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The crystal and molecular structures are reported for two isomeric imidazoles: 1-methyl-2-phenylimidazole (1) and 1-methyl-4-phenylimidazole (2). In molecule 2 the phenyl ring is rotated by 7.3-degrees from the heterocyclic plane due to steric interactions. The steric congestion is much more severe in 1, with the adjacent methyl and phenyl substituents mininizing nonbonded interactions via a 32.3-degrees rotation of the phenyl ring and a 0.159 angstrom displacement of the methyl carbon from the heterocyclic plane.

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页码：899 / 901

页数：3

相关论文

共 11 条

[1] MODEL COMPOUNDS FOR R-STATE AND T-STATE HEMOGLOBINS [J].

GEIBEL, J ;

CANNON, J ;

CAMPBELL, D ;

TRAYLOR, TG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3575-3585

[2] STRUCTURE OF 1-(4-IMIDAZOLYLSULFONYL)-4-PHENYLIMIDAZOLE [J].

GUGGENBERGER, LJ .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 1975, 31 (JAN15) :13-19

[3]

ILGENFRITZ G, 1974, J BIOL CHEM, V249, P2959

[4] LINEAR FREE-ENERGY RELATIONSHIPS IN BINDING OF OXYGEN AND CARBON-MONOXIDE WITH HEME MODEL COMPOUNDS AND HEME-PROTEINS [J].

LAVALETTE, D ;

TETREAU, C ;

MISPELTER, J ;

MOMENTEAU, M ;

LHOSTE, JM .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1984, 145 (03) :555-565

[5] KINETIC-STUDY OF HALIDE IONIZATION FROM COBALT(III) PORPHYRIN COMPLEXES - RATE ENHANCEMENTS PRODUCED BY HYDROGEN-BONDING TO THE HALIDE AND BY STERIC CONGESTION FROM COORDINATED 2-SUBSTITUTED IMIDAZOLES [J].

MAHMOOD, A ;

LIU, HL ;

JONES, JG ;

EDWARDS, JO ;

SWEIGART, DA .

INORGANIC CHEMISTRY, 1988, 27 (12) :2149-2154

[6] 1-(2-PYRIDYL)-5-METHYLIMIDAZOLE [J].

MENTE, DC ;

SUNDBERG, RJ ;

BRYAN, RF .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (DEC) :3923-3926

[7] STEREOCHEMISTRY OF COOPERATIVE MECHANISMS IN HEMOGLOBIN [J].

PERUTZ, MF ;

FERMI, G ;

LUISI, B ;

SHAANAN, B ;

LIDDINGTON, RC .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (09) :309-321

[8] CHEMISTRY OF THE PHENOXATHIINS AND ISOSTERICALLY RELATED HETEROCYCLES .29. THE CRYSTAL AND MOLECULAR-STRUCTURE OF 5-(3'-HYDROXYPYRIDYL-2'-THIO)-4-NITRO-1-METHYLIMIDAZOLE [J].

PUIGTORRES, S ;

MARTIN, GE ;

LARSON, SB ;

SIMONSEN, SH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (01) :155-159

[9] KINETICS AND MECHANISMS OF CARBON-MONOXIDE DISSOCIATION FROM CHELATED HEME-CO COMPLEXES - MODELS FOR HEMOPROTEIN REACTIONS [J].

TRAYLOR, TG ;

CAMPBELL, D ;

SHARMA, V ;

GEIBEL, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) :5376-5383

[10] CRYSTAL AND MOLECULAR STRUCTURE OF 4-ACETYLAMINO-2-BROMO-5-ISOPROPYL-1-METHYLIMIDAZOLE [J].

VANREMOORTERE, FP ;

BOER, FP .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (05) :976-+