Toward the Complete Prediction of the <sup>1</sup>H and <sup>13</sup>C NMR Spectra of Complex Organic Molecules by DFT Methods: Application to Natural Substances

Chemistry - A European Journal - Tập 12 Số 21 - Trang 5514-5525 - 2006
Alessandro Bagno1, Federico Rastrelli1, Giacomo Saielli2
1Dipartimento di Scienze Chimiche, Università di Padova, Italy, Fax: (+39)‐049‐8275239
2Istituto per la Tecnologia delle Membrane del CNR, Sezione di Padova, Via Marzolo, 1, 35131 Padova, Italy

Tóm tắt

AbstractThe NMR parameters (1H and 13C chemical shifts and coupling constants) for a series of naturally occurring molecules have been calculated mostly with DFT methods, and their spectra compared with available experimental ones. The comparison includes strychnine as a test case, as well as some examples of recently isolated natural products (corianlactone, daphnipaxinin, boletunone B) featuring unusual and/or crowded structures and, in the case of boletunone B, being the subject of a recent revision. Whenever experimental spectra were obtained in polar solvents, the calculation of NMR parameters was also carried out with the Integral Equation‐Formalism Polarizable Continuum Model (IEF‐PCM) continuum method. The computed results generally show a good agreement with experiment, as judged not only by statistical parameters but also by visual comparison of line spectra. The origin of the remaining discrepancies is attributed to the incomplete modeling of conformational and specific solvent effects.

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Tài liệu tham khảo

 

10.1002/ange.200460864

10.1002/anie.200460864

10.1002/mrc.972

10.1016/S0079-6565(98)00022-3

10.1021/ol990725b

10.1016/j.pnmrs.2005.06.001

10.1021/cr960017t

10.1016/S0079-6565(02)00050-X

10.1016/S0066-4103(03)51004-3

2004, Calculation of NMR and EPR Parameters

10.1002/mrc.1312

Case D. A., 2004, Calculation of NMR and EPR Parameters

 

10.1021/ja994544g

10.1021/jp9937050

10.1021/jp004530t

10.1021/jo010985i

10.1021/ol0200347

10.1021/jo035400u

10.1002/1521-3765(20010417)7:8<1652::AID-CHEM16520>3.0.CO;2-V

10.1021/jp0353284

10.1021/ja021237t

10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0

10.1002/1521-3765(20020715)8:14<3240::AID-CHEM3240>3.0.CO;2-G

10.1002/mrc.1410

10.1021/ol026310z

10.1021/ol049913e

 

10.1002/mrc.1064

10.1002/ejoc.200500473

10.1002/chem.200306065

 

10.1002/ange.200460336

10.1002/anie.200460336

10.1021/jp990523x

 

10.1016/S0022-2860(84)87198-7

Ö.Farkas PhD (CsC) Thesis Eötvös Loránd University and Hungarian Academy of Sciences Budapest (Hungary) 1995;

10.1063/1.480484

 

10.1063/1.474659

10.1016/S0009-2614(98)00106-7

10.1063/1.473558

Gaussian 03 (Revision A.1) M. J. Frisch G. W. Trucks H. B. Schlegel G. E. Scuseria M. A. Robb J. R. Cheeseman J. A. Montgomery Jr. T. Vreven K. N. Kudin J. C. Burant J. M. Millam S. S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G. A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J. E. Knox H. P. Hratchian J. B. Cross C. Adamo J. Jaramillo R. Gomperts R. E. Stratmann O. Yazyev A. J. Austin R. Cammi C. Pomelli J. W. Ochterski P. Y. Ayala K. Morokuma G. A. Voth P. Salvador J. J. Dannenberg V. G. Zakrzewski S. Dapprich A. D. Daniels M. C. Strain O. Farkas D. K. Malick A. D. Rabuck K. Raghavachari J. B. Foresman J. V. Ortiz Q. Cui A. G. Baboul S. Clifford J. Cioslowski B. B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R. L. Martin D. J. Fox T. Keith M. A. Al‐Laham C. Y. Peng A. Nanayakkara M. Challacombe P. M. W. Gill B. Johnson W. Chen M. W. Wong C. Gonzalez and J. A. Pople Gaussian Inc. Wallingford CT 2004.

 

10.1063/1.464913

10.1103/PhysRevB.37.785

10.1103/PhysRevLett.77.3865

10.1002/jcc.1056

 

10.1103/PhysRevA.38.3098

10.1103/PhysRevB.33.8822

10.1006/jmre.1998.1453

10.1016/0022-2364(74)90181-4

10.1139/v83-299

10.1002/(SICI)1097-458X(199908)37:8<517::AID-MRC501>3.0.CO;2-W

10.1002/mrc.1447

10.1006/jmra.1995.0021

10.1021/np50045a013

10.1006/jmra.1994.1077

10.1002/mrc.1623

10.1016/j.jmr.2003.09.011

10.1002/mrc.1260320214

10.1006/jmra.1996.0083

10.1006/jmre.2000.2205

10.1002/mrc.902

10.1021/ol049660p

10.1107/S0108768102003890

10.1021/ol049756j

 

10.1063/1.1566734

10.1021/jp046334i

 

10.1021/jp010837w

10.1021/jp044781s

10.1021/ol049953i

10.1021/ol048724t

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Chemistry - A European Journal

Tập 12 Số 21

5514-5525

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