A Multi-standard Approach for GIAO 13C NMR Calculations

被引：205

作者：

Sarotti, Ariel M. ^{[1
]}

Pellegrinet, Silvina C. ^{[1
]}

机构：

[1] Univ Nacl Rosario, CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, RA-2000 Rosario, Santa Fe, Argentina

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 19期

关键词：

DENSITY-FUNCTIONAL METHODS; PROTON CHEMICAL-SHIFTS; AB-INITIO METHODS; STEREOSTRUCTURE ASSIGNMENT; CONFORMATIONAL-ANALYSIS; NATURAL-PRODUCTS; STRUCTURAL REASSIGNMENT; RELATIVE CONFIGURATION; SHIELDING CONSTANTS; STRUCTURE REVISION;

D O I：

10.1021/jo901234h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The influence of the reference standard employed in the calculation of C-13 NMR chemical shifts was investigated over a large variety of known organic compounds, using different quantum chemistry methods and basis sets. After detailed analysis of the collected data, we found that methanol and benzene are excellent reference standards For computing NMR shirts of sp(3)- and sp-sp(2)-hybridized carbon atoms, respectively. This multi-standard approach (MSTD) performs better than TMS in terms of accuracy and precision and also displays much lower dependence oil the level of theory employed. The use of mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level is recommended for accurate C-13 NMR chemical shift prediction at low computational cost.

引用

收藏

页码：7254 / 7260

页数：7

相关论文

共 64 条

[1] Exchange functionals with improved long-range behavior and adiabatic connection methods without adjustable parameters:: The mPW and mPW1PW models [J].

Adamo, C ;

Barone, V .

JOURNAL OF CHEMICAL PHYSICS, 1998, 108 (02) :664-675

[2] Isolation and structure determination of aplidinones A-C from the Mediterranean ascidian Aplidium conicum:: A successful regiochemistry assignment by quantum mechanical 13C NMR chemical shift calculations [J].

Aiello, A ;

Fattorusso, E ;

Luciano, P ;

Mangoni, A ;

Menna, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (23) :5024-5030

[3] Structural Reassignment, Absolute Configuration, and Conformation of Hypurticin, a Highly Flexible Polyacyloxy-6-heptenyl-5,6-dihydro-2H-pyran-2-one [J].

Alberto Mendoza-Espinoza, Jose ;

Lopez-Vallejo, Fabian ;

Fragoso-Serrano, Mabel ;

Pereda-Miranda, Rogelio ;

Cerda-Garcia-Rojas, Carlos M. .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (04) :700-708

[4] Scaling factors for carbon NMR chemical shifts obtained from DFF B3LYP calculations [J].

Aliev, Abil E. ;

Courtier-Murias, Denis ;

Zhou, Shen .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2009, 893 (1-3) :1-5

[5] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134

[6] Theoretical and experimental investigation of the 1H NMR spectrum of putrescine [J].

Allouche, A. R. ;

Graveron-Demilly, D. ;

Fauvelle, F. ;

Aubert-Frecon, M. .

CHEMICAL PHYSICS LETTERS, 2008, 466 (4-6) :219-222

[7]

[Anonymous], HYP PROF REL 7 52

[8]

[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014

[9] Toward the complete prediction of the 1H and 13C NMR spectra of complex organic molecules by DFT methods:: Application to natural substances [J].

Bagno, Alessandro ;

Rastrelli, Federico ;

Saielli, Giacomo .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5514-5525

[10] Correlation of empirical δ(TMS) and absolute NMR chemical shifts predicted by ab initio computations [J].

Baldridge, KK ;

Siegel, JS .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (20) :4038-4042

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