ECLIPSED GROUND-STATE CONFORMATIONS FOR METHOXYCYCLOHEXANES WITH ADJACENT METHYL-GROUP SUBSTITUTION - AN NMR CRITERION AND MOLECULAR MECHANICS CALCULATIONS

被引：26

作者：

ANDERSON, JE

IJEH, AI

机构：

[1] Chemistry Department, University College, London, WC1E 6BT, Gower Street

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 09期

关键词：

D O I：

10.1039/p29940001965

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molecular mechanics calculations suggest that the conformation of the ring-to-oxygen bond in several methoxycyclohexanes with equatorial methyl substituents in both the 2- and 6-positions is eclipsed. The three bond coupling constant of the methine proton with the methoxy carbon, which is large compared with that of methoxycyclohexane. confirms this and is diagnostic of an eclipsed conformation. The corresponding acyclic compound 2,4-dimethyl-3-methoxypentane is also concluded to have an eclipsed C-O bond.

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页码：1965 / 1967

页数：3

相关论文

共 40 条

[1] MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].

ALLINGER, NL ;

YUH, YH ;

LII, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566

[2] A MOLECULAR MECHANICS FORCE-FIELD (MM3) FOR ALCOHOLS AND ETHERS [J].

ALLINGER, NL ;

RAHMAN, M ;

LII, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8293-8307

[3]

ANDERSON J, UNPUB

[4] THE 6 ECLIPSED SIDE-CHAINS IN SCYLLO-INOSITOL HEXAMETHYL ETHER - A MOLECULAR MECHANICS STUDY [J].

ANDERSON, JE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03) :441-443

[5] ECLIPSED CONFORMATIONS OF 1,1,2-TRISUBSTITUTED SINGLE BONDS WITH SPACE-DEMANDING SUBSTITUENTS - EXAMPLES FROM X-RAY-DIFFRACTION STRUCTURE DETERMINATIONS [J].

ANDERSON, JE ;

WATSON, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1517-1518

[6] THE NONALTERNATING GROUND-STATE CONFORMATIONS OF SOME SIMPLE ECLIPSED CARBON CARBON AND NITROGEN CARBON BONDS - X-RAY CRYSTALLOGRAPHIC EVIDENCE AND MOLECULAR MECHANICS CALCULATIONS [J].

ANDERSON, JE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (08) :1343-1345

[7] THE MEASUREMENT OF THE ONE-FOLD ROTATIONAL BARRIER OF ECLIPSED BONDS - A DYNAMIC NMR DETERMINATION OF N-O OR N-CH2 BOND ROTATION IN N-ALKOXY-2,2,6,6-TETRAMETHYLPIPERIDINES OR N-ALKYL-2,2,6,6-TETRAMETHYLPIPERIDINES [J].

ANDERSON, JE ;

CASARINI, D ;

CORRIE, JET ;

LUNAZZI, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (07) :1299-1304

[8] THE ECLIPSED NON-ALTERNATING GROUND-STATE CONFORMATION FOR 1,1,2-TRI-TRANS-BUTYLETHANE - MOLECULAR MECHANICS CALCULATIONS AND NMR-SPECTRUM [J].

ANDERSON, JE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (03) :299-302

[9]

ANDERSON JE, 1993, J AM CHEM SOC, V115, P3493

[10]

ANDERSON JE, 1992, CHEM ALKANES CYCLOAL

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