Relative stabilities and conformational ring inversion potentials in heterocyclic decalin systems and stereoelectronic implications

被引:7
作者
Golender, L [1 ]
Senderowitz, H [1 ]
Fuchs, B [1 ]
机构
[1] TEL AVIV UNIV, SCH CHEM, IL-69978 TEL AVIV, ISRAEL
来源
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 1996年 / 370卷 / 2-3期
基金
以色列科学基金会;
关键词
computations; conformational analysis; dioxadecalins; oxadecalins; stereoelectronics; tetraoxadecalins; trioxadecalins;
D O I
10.1016/S0166-1280(96)04704-5
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The energy differences between stereoisomers and the ring inversion potential surfaces of decalin (1) and various oxadecalins (2, 3), dioxadecalins (4-7), trioxadecalins (8, 9) and tetraoxadecalins (10, 11) were interrogated following the generally accepted scheme of a stepwise conformational six-ring inversion process and using molecular mechanics techniques (MM3 and MM3-GE, i.e. MM3 reparametrized for treatment of the ''gauche effect''). The results were compared with some available experimental data and were also used to probe the validity of a recently elaborated protocol for ring-fragment analysis of oxygen-containing bicyclic systems in terms of their interannular fragment components: C-C-C-C, C-C-C-O, C-C-O-C, C-O-C-O-C and O-C-C-O, the latter two with their corresponding stereoelectronic effects, namely, the ''anomeric effect'' and the ''gauche effect'', respectively.
引用
收藏
页码:221 / 236
页数:16
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