Analysis of the origin of through-space proton NMR deshielding by selected organic functional groups

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3823-3824

  Martin, Ned H ^a   Brown, Justin D ^a   Nance, Kimberly H ^a   Schaefer III, Henry F ^b   Schleyer, Paul V R ^b   Wang, Zhi Xiang ^b   Woodcock, H Lee ^b  

^a UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

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ARTICLE;

EID: 0001684280     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016500u     Document Type: Article

References (16)

1. Günther, H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry, 2nd ed.; Wiley: Chichester, 1995; pp 78-84.
2. McConnell, H. M. J. Chem. Phys. 1957, 27, 226-229.
3. (a) Martin, N. H.; Allen, N. W., III; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. J. Am. Chem. Soc. 1998, 120, 11510-11511.
4. (b) Martin, N. H.; Allen, N. W., III; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. Struct. Chem. 1998, 9(6), 403-410.
5. (c) Alkorta, I.; Elguero, J. New J. Chem. 1998, 22, 381-385.
6. (d) Martin, N. H.; Allen, N. W., III; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. In Modeling NMR Chemical Shifts: Gaining Insights into Structure and Environment; Facelli, J. C., deDios, A. C., Eds.; ACS Symposium Series 732; American Chemical Society: Washington, DC, 1999; pp 207-219.
7. (e) Martin, N. H.; Allen, N. W., III; Minga, E. K.; Ingrassia, S. T.; Brown, J. D. Struct. Chem. 1999, 10(5), 375-380.
8. (f) Attention is called to a related, recent study on ethene, acetylene, HCN, and formaldehyde: Klod, S.; Kleinpeter, E. J. Chem. Soc., Perkin Trans. 2 2001, advance article.
9. Martin, N. H.; Allen, N. W., III; Brown, J. D.; Ingrassia, S. T.; Minga, E. K. J. Mol. Graphics Mod. 2000, 18(1), 1-6.
10. (a) IGLO program. See: Fleischer, U.; Kutzelnigg, W.; Lazzeretti, P.; Muehlenkamp, V. J. Am. Chem. Soc. 1994, 116, 5298.
11. (b) DeMon program: Malkin, V. G.; Malkina, O. L.; Casida, M. E.; Salahub, D. R. J. Am. Chem. Soc. 1994, 116, 5898.
12. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford. S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; AlLaham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussain, Inc.: Pittsburg, PA, 1998.
13. Quantum chemical programs compute absulote shieldings (but not chemical shifts) directly. More positive values mean greater shielding (i.e., the resonances are more upfield). Note that the signs are reversed in the NMR chemical shift convention: more positive chemical shifts are downfield. Thus, NICS is based on the negative of the absulote shieldings computed at selected points in space designated by "ghost atoms" (Bq's).
14. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317-6318.
15. (b) Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669.
16. (c) Scheleyer, P. v. R.; Manoharan, M.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. v. E. Org Lett. 2001, 3(16), 2465-2468.