Computed NMR shielding increments over unsaturated five-membered ring heterocyclic compounds as a measure of aromaticity

Journal of Molecular Graphics and Modelling

Volumn 27, Issue 8, 2009, Pages 853-859

  Martin, Ned H ^a   Rowe, Jimmy E ^a   Pittman, Eddie LaReece ^a  

^a UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

Author keywords

Aromaticity; Conjugated five membered heterocyclic rings; GIAO; NMR shielding

Indexed keywords

AROMATIC STABILIZATION ENERGIES; AROMATICITY; CARTESIAN COORDINATE; CONJUGATED FIVE-MEMBERED HETEROCYCLIC RINGS; FIVE-MEMBERED RINGS; GAUSSIAN; GIAO; HARMONIC OSCILLATOR MODEL OF AROMATICITY; HETEROCYCLIC COMPOUND; ISOTROPIC SHIELDING; NMR SHIELDING; NUCLEUS-INDEPENDENT CHEMICAL SHIFTS; PHOSPHOLE; PROBE POSITION;

AROMATIZATION; HYDROGEN; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC POLYMERS; OSCILLATORS (ELECTRONIC); OSCILLATORS (MECHANICAL); PROBES; SPACE PROBES; THIOPHENE; UNSATURATED COMPOUNDS;

SHIELDING;

AROMATIC COMPOUND; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; PHOSPHOLE DERIVATIVE; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; ENERGY TRANSFER; MAGNETISM; NORMAL DISTRIBUTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

FURANS; HETEROCYCLIC COMPOUNDS; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXAZOLES; PYRAZOLES; PYRROLES;

EID: 67349150488     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2009.01.002     Document Type: Article

References (38)

1. Kekulé A. Sur la constitution des substances aromatiques. Bull. Soc. Chim. Fr. (Paris) 3 2 (1865) 98-110
2. Schleyer P.V.R. Introduction: aromaticity. Chem. Rev. 101 5 (2001) 1115-1118
3. Krygowski T.M. Crystallographic studies of inter- and intramolecular interactions reflected in aromatic character of π-electron systems. J. Chem. Inf. Comput. Sci. 33 1 (1993) 70-78
4. Krygowski T.M., and Cyrański M.K. Separation of the energetic and geometric contributions to the aromaticity of π-electron carbocyclics. Tetrahedron 52 5 (1996) 1713-1722
5. Krygowski T.M., and Cyrański M.K. Aromatic character of carbocyclic π-electron systems deduced from molecular geometry. In: Hargittai M., and Hargittai I. (Eds). Advances in Molecular Structure Research vol. 3 (1997), JAI Press, London 227-268
6. Krygowski T.M., and Cyrański M.K. Structural aspects of aromaticity. Chem. Rev. 101 5 (2001) 1385-1419
7. Hehre W.J., McIver R.T., Pople J.A., and Schleyer P.V.R. Alkyl substituent effects on the stability of protonated benzene. J. Am. Chem. Soc. 96 (1974) 7162-7163
8. George P., Trachtman M., Brett A.M., and Bock C.W. Comparison of various isodesmic and homodesmotic reaction heats with values derived from published ab initio molecular orbital calculations. J. Chem. Soc., Perkin Trans. 2 (1977) 1036-1047
9. Suresh C.H., and Koga N. Accurate calculation of aromaticity of benzene and antiaromaticity of cyclobutadiene: new homodesmotic reactions. J. Org. Chem. 67 (2002) 1965-1968
10. Schaad L.J., and Hess Jr. B.A. Dewar resonance energy. Chem. Rev. 101 5 (2001) 1465-1476
11. Liebman J.F., and Slayden S.W. The energetics of aromatic hydrocarbons: an experimental thermochemical perspective. Chem. Rev. 101 5 (2001) 1541-1566
12. Dauben H.J., Wilson J.D., and Laity J.L. Diamagnetic susceptibility exaltation as a criterion of aromaticity. J. Am. Chem. Soc. 91 8 (1969) 1991-1998
13. Hoarau J. Magnetic properties of conjugated molecules. J. Ann. Chim. 13 1 (1956) 544-587
14. Pacault A. Magnetochemical studies A. Ann. Chim. 12 1 (1946) 527-587
15. Flygare W.H. Magnetic interactions in molecules and an analysis of molecular electronic charge distribution from magnetic parameters. Chem. Rev. 74 (1974) 653-687
16. Haigh C.W., and Mallion R.B. Ring current theories in nuclear magnetic resonance. In: Emsley J.W., Feeny J., and Sutcliffe L.H. (Eds). Progress in Nuclear Magnetic Resonance Spectroscopy, vol. 13 (1979-1980), Pergamon Press, Oxford, UK
17. Gomes J.A.N.F., and Mallion R.B. The concept of ring currents. In: Rouvray D.H. (Ed). Concepts in Chemistry: A Contemporary Challenge (1997), Research Studies Press, Taunton, Somerset, UK 205-253
18. Lazzeretti P. Ring currents. In: Emsley J.W., Feeny J., and Sutcliffe L.H. (Eds). Progress in Nuclear Magnetic Resonance Spectroscopy vol. 36 (2000), Elsevier, Amsterdam, The Netherlands 1-88
19. Schleyer P.V.R., Maerker C., Dransfield A., Jiao H., and van Eikema Hommes N.J.R. Nucleus-independent chemical shifts: a simple and efficient aromaticity probe. J. Am. Chem. Soc. 118 (1996) 6317-6318
20. Chen Z., Wannere C.S., Corminboeuf C., Puchta R., and Schleyer P.V.R. Nucleus-independent chemical shifts (NICS) as an aromaticity criterion. Chem. Rev. 105 10 (2001) 3842-3888
21. Jusélius J., and Sundholm D. Ab initio determination of the induced ring current in aromatic molecules. Phys. Chem. Chem. Phys. 1 (1999) 3429-3435
22. Klod S., and Kleinpeter E. Ab initio calculation of the anisotropy effect of multiple bonds and the ring current effect of arenes-application in conformational and configurational analysis. J. Chem. Soc. Perkin Trans. 2 (2001) 1893-1898
23. Kleinpeter E., and Klod S. Ab initio calculation of the anisotropic/ring current effects of amino acid residues to locate the position of substrates in the binding site of enzymes. J. Mol. Struct. 704 (2004) 79-82
24. Stanger A. Nucleus-independent chemical shifts (NICS): distance dependence and revised criteria for aromaticity and antiaromaticity. J. Org. Chem. 71 3 (2006) 883-893
25. Cyrański M.K., Krygowski T.M., Katritsky A.R., and Schleyer P.V.R. To what extent can aromaticity be defined uniquely?. J. Org. Chem. 67 4 (2002) 1333-1338
26. Cyrański M.K. Energetic aspects of cyclic pi-electron delocalization: evaluation of the methods of estimating aromatic stabilization energies. Chem. Rev. 105 10 (2005) 3773-3811 (and references cited therein)
27. Martin N.H., Loveless D.M., Main K.L., and Wade D.C. Computation of through-space NMR shielding effects by small-ring aromatic and antiaromatic hydrocarbons. J. Mol. Graphics Modell. 25 (2006) 389-395
28. Martin N.H., Floyd R.M., Woodcock H.L., Huffman S., and Lee C.-K. Computation of through-space NMR shielding effects in aromatic ring Pi-stacked complexes. J. Mol. Graphics Modell. 26 (2008) 1125-1130
29. Martin N.H., Caldwell B.W., Carlson K.P., and Teague M.R. Ab initio calculation of through-space magnetic shielding of linear polycyclic aromatic hydrocarbons (acenes): extent of aromaticity. J. Mol. Graphics Modell. 27 (2009) 689-692
30. Titan, Version 1.0.1 (1999), Wavefunction Inc., Schrödinger Inc.
31. Hehre W.J., Radom L., Schleyer P.V.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley, New York
32. Martin N.H., Loveless D.M., and Wade D.C. A comparison of the calculated NMR shielding probes. J. Mol. Graphics Modell. 23 (2004) 285-290
33. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.01 (2003), Gaussian Inc., Pittsburgh, PA
34. Boys S.F., and Bernardi F. The calculations of small molecular interaction by the difference of separate total energies. Some procedures with reduced error. Mol. Phys. 19 (1970) 553-566
35. TableCurve3D, Version 3.00A (1997), AISN Software, San Rafael, CA
36. Chauvin R. Explicit periodic trend of van der Waals radii. J. Phys. Chem. 96 (1992) 9194-9197
37. P.V.R. Schleyer, Private communication.
38. Martin N.H., Brown J.D., Nance K.H., Schaefer III H.F., Schleyer P.V.R., Wang Z.-X., and Woodcock H.L. Analysis of the origin of through-space NMR (de)shielding by selected organic functional groups. Org. Lett. 3 24 (2001) 3823-3826