Quantum mechanical calculations of NMR J coupling values in the determination of relative configuration in organic compounds

被引：61

作者：

Bifulco, G ^{[1
]}

Bassarello, C ^{[1
]}

Riccio, R ^{[1
]}

Gomez-Paloma, L ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Fisciano, SA, Italy

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 06期

关键词：

D O I：

10.1021/ol049913e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach relying on quantum mechanical calculations of proton-proton and proton-carbon J coupling values is proposed as a tool for assigning the relative configuration on chiral organic compounds. The method is suitable for carbon frameworks containing several adjacent stereogenic centers and may allow significant advances in the extensive use of spin-spin couplings in structural elucidation.

引用

页码：1025 / 1028

页数：4

共 21 条

[1] Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters:: The mPW and mPW1PW models
Adamo, C
Barone, V
[J]. JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (02) : 664 - 675
[2] Predicting 13C NMR spectra by DFT calculations
Bagno, A
Rastrelli, F
Saielli, G
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (46) : 9964 - 9973
[3] Barone G, 2002, CHEM-EUR J, V8, P3233, DOI 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO
[4] 2-0
[5] Barone G, 2002, CHEM-EUR J, V8, P3240, DOI 10.1002/1521-3765(20020715)8:14<3240::AID-CHEM3240>3.0.CO
[6] 2-G
[7] Simulation of 2D 1H homo- and 1H-13C heteronuclear NMR spectra of organic molecules by DFT calculations of spin-spin coupling constants and 1H and 13C-chemical shifts
Bassarello, C
Cimino, P
Gomez-Paloma, L
Riccio, R
Bifulco, G
[J]. TETRAHEDRON, 2003, 59 (48) : 9555 - 9562
[8] Bassarello C, 2001, EUR J ORG CHEM, V2001, P39, DOI 10.1002/1099-0690(200101)2001:1<39::AID-EJOC39>3.0.CO
[9] 2-9
[10] Stereochemical studies on ascaulitoxin:: a J-based NMR configurational analysis of a nitrogen substituted system
Bassarello, C
Bifulco, G
Evidente, A
Riccio, R
Gomez-Paloma, L
[J]. TETRAHEDRON LETTERS, 2001, 42 (49) : 8611 - 8613

← 1 2 3 →