Nuclear magnetic resonance and molecular orbital study of some cocaine analogues

被引：7

作者：

Airaksinen, AJ

Tuppurainen, KA

Lötjönen, SE

Niemitz, M

Yu, MX

Vepsäläinen, JJ

Laatikainen, R

Hiltunen, J

Bergström, KA

机构：

[1] Univ Kuopio, Dept Chem, FIN-70211 Kuopio, Finland

[2] MAP Med Technol OY, FIN-41160 Tikkakoski, Finland

[3] Kuopio Univ Hosp, Dept Clin Physiol & Nucl Med, FIN-70211 Kuopio, Finland

来源：

TETRAHEDRON | 1999年 / 55卷 / 34期

关键词：

cocaine analogues; conformation; molecular modelling; NMR;

D O I：

10.1016/S0040-4020(99)00577-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

H-1 NMR spectra of (-)-cocaine and some of its derivatives (alpha-CPT, beta-CPT, nor-beta-CIT, cocaine-HCl and ecgonine-HCl) were analysed and the spectral parameters were used for conformational analysis of the compounds in conjunction with theoretical HF/6-31G*. MMP2, AMI and molecular dynamics calculations. Comparison of the experimental and theoretical data reveals that the compounds are predominantly in a rigid chair conformation, which is rather similar for all compounds. No large differences were found in the dynamical behaviour of the molecules. The performance of the Haasnoot and Altona equations is discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：10537 / 10546

页数：10

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