RESTRICTED ROTATION AND NOE TRANSFER - A CONFORMATIONAL STUDY OF SOME SUBSTITUTED (9-ANTHRYL)CARBINOL DERIVATIVES

被引：31

作者：

DERIGGI, I ^{[1
]}

VIRGILI, A ^{[1
]}

DEMORAGAS, M ^{[1
]}

JAIME, C ^{[1
]}

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BARCELONA,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 01期

关键词：

D O I：

10.1021/jo00106a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four alkyl- and aryl(9-anthryl)carbinols (methyl, isopropyl, tert-butyl, and phenyl) were synthesized and revealed restricted rotation about the C-9-C-11 bond. Their free energy of activation for rotation has been determined, being 11.0, 14.0, 21.7, and 9.8 kcal/mol, respectively. The application of NOE enhancement and relaxation time measurements for the determination of the activation energy for bond rotation is described. The good agreement with the values obtained with the coalescence temperature method bears out that the NOE based approach is a good alternative for the determination of high rotational barriers. Molecular Mechanics (MM2) calculations give values close to the experimental ones.

引用

页码：27 / 31

页数：5

共 22 条

[1]

Allinger N. L., 1980, QCPE, P395

[2] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[3]

BENHASSINE B, 1985, B SOC CHIM BELG, V94, P425

[4] CONFORMATIONAL STUDIES BY DYNAMIC NMR .37. MONITORING THE STEREOMUTATIONS OF SYMMETRIC AMINES BY MEANS OF A CHIRAL AUXILIARY AGENT [J].

CASARINI, D ;

DAVALLI, S ;

LUNAZZI, L ;

MACCIANTELLI, D .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4616-4619

[5]

FALLER JW, 1973, DETERMINATION ORGANI, V5

[6] COMPLETE ENERGY PROFILE OF A CHIRAL PROPELLER COMPOUND - TRIS-(2'-METHYLBENZIMIDAZOL-1'-YL)METHANE (TMBM) - CHROMATOGRAPHIC RESOLUTION ON TRIACETYL CELLULOSE, X-RAY STRUCTURES OF THE RACEMIC AND ONE ENANTIOMER, AND DYNAMIC NMR-STUDY [J].

FOCESFOCES, C ;

CANO, FH ;

MARTINEZRIPOLL, M ;

FAURE, R ;

ROUSSEL, C ;

CLARAMUNT, RM ;

LOPEZ, C ;

SANZ, D ;

ELGUERO, J .

TETRAHEDRON-ASYMMETRY, 1990, 1 (02) :65-86

[7]

HOFFMAN RA, 1966, PROG NMR SPECTROSC, V1, P89

[8] CONFORMATIONAL STUDY OF (R)-(-)-2,2,2-TRIFLUORO-1-(9-ANTHRYL)ETHANOL (PIRKLE ALCOHOL) BY DYNAMIC NMR [J].

JAIME, C ;

VIRGILI, A ;

CLARAMUNT, RM ;

LOPEZ, C ;

ELGUERO, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6521-6523

[9]

LIPKOWITZ KB, 1987, ANAL CHEM, V59, P1733

[10]

NEUHAUS D, 1989, NUCLEAR OVERHAUSER E

← 1 2 3 →