Conformational analysis with carbon-carbon coupling constants. A density functional and molecular mechanics study

被引：27

作者：

Stahl, M ^{[1
]}

Schopfer, U ^{[1
]}

Frenking, G ^{[1
]}

Hoffmann, RW ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 11期

关键词：

D O I：

10.1021/jo970061o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For a 1,3-dimethylated model compound (1), (3)J(CC) coupling constants were calculated by a density functional (SOS-DFPT/IGLO) method using molecular mechanics as well as ab initio optimized geometries. Boltzmann averaging of the calculated coupling constants for individual conformers resulted in good agreement with the experimental data. The comparison to calculated values allows a more quantitative interpretation of the experimental coupling constants for the conformational analysis of open chain compounds.

引用

页码：3702 / 3704

页数：3

共 26 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] CONFORMATIONAL AND SUBSTITUENT DEPENDENCIES OF C-13-C-13 COUPLING-CONSTANTS [J].

BARFIELD, M ;

BURFITT, I ;

DODDRELL, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (10) :2631-2634

[3] THE CONFORMATIONAL DEPENDENCE OF VICINAL C-13-C-13 SPIN-SPIN COUPLING-CONSTANTS IN ALICYCLIC COMPOUNDS [J].

BERGER, S .

ORGANIC MAGNETIC RESONANCE, 1980, 14 (01) :65-68

[4] ABINITIO QUADRATIC CONFIGURATION-INTERACTION CALCULATION OF INDIRECT NMR SPIN-SPIN COUPLING-CONSTANTS [J].

CARMICHAEL, I .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (09) :1789-1792

[5] AN INTERNAL COORDINATE MONTE-CARLO METHOD FOR SEARCHING CONFORMATIONAL SPACE [J].

CHANG, G ;

GUIDA, WC ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4379-4386

[6] CALCULATION OF NUCLEAR SPIN-SPIN COUPLING-CONSTANTS WITH AB-INITIO MOLECULAR-ORBITAL WAVE-FUNCTIONS [J].

EDISON, AS ;

MARKLEY, JL ;

WEINHOLD, F .

JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (45) :11657-11665

[7]

FACKE T, 1995, J AM CHEM SOC, V117, P9547

[8]

Frisch M.J., 1995, GAUSSIAN 94

[9] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[10]

Hoffmann R W., 1992, Angewandte Chemie International Ed, V104, P1147, DOI DOI 10.1002/ANGE.19921040905

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