15N NMR chemical shifts of ring substituted benzonitriles

Magnetic Resonance in Chemistry

Volumn 44, Issue 12, 2006, Pages 1073-1080

  Žéček, Petr ^a   Dransfeld, Alk ^b   Exner, Otto ^c   Schraml, Jan ^a  

^a INSTITUTE OF CHEMICAL PROCESS FUNDAMENTALS   (Czech Republic)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^c INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

13C benzonitriles; 15N; 1J(15N 13C); Ab initio calculations; Chemical shifts; DSP analysis; Hammett correlation; Magnetic susceptibility; NMR; PCA treatment; SCS

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL SHIFT; QUANTUM CHEMISTRY;

13C BENZONITRILE; 15N; 1J(15N-13C); AB INITIO CALCULATIONS; BENZONITRILES; DSP ANALYSE; HAMMETT CORRELATION; NMR CHEMICAL SHIFTS; PCA TREATMENT; SCS;

MAGNETIC SUSCEPTIBILITY;

EID: 33845236642     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.1900     Document Type: Article

References (48)

1. Pregosin PS, Randall EW, White AI. J. Chem. Soc., Perkin Trans. 2 1972; 513.
2. 3 and give incorrect shift in 4-CN derivative, the correct value is -114.0).
3. Kutzelnigg W, Fleischer U, Schindler M. The IGLO Method in NMR Basic Principles and Progress, vol 23, Diehl P, Fluck E, Kosfeld R (eds). Springer: Berlin, 1990; 165.
4. Chesnut DB. Chem. Phys. Lett. 2003; 380: 251.
5. Wrackmeyer B, Köhler C. Heteroat. Chem. 2005; 16: 84.
6. Craik DJ, Levy GC, Brownlee RTC. J. Org. Chem. 1983; 48: 1601.
7. Ehrenson S, Brownlee RTC, Taft RW. Prog. Phys. Org. Chem. 1973; 10: 1.
8. Exner O, Buděšínsky M. Magn. Reson. Chem. 1989; 27: 27.
9. Exner O, Boček K. Collect. Czech. Chem. Commun. 1973; 38: 50.
10. Witanowski M, Stefaniak L, Szymanski S, Januszewski H. J. Magn. Reson. 1977; 28: 217.
11. Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1993; 25: 1.
12. Harris RK, Becker ED, De Menzes SMC, Goodfellow R, Granger P. Pure Appl. Chem. 2001; 73: 1795.
13. Homer J. J. Magn. Reson. 1984; 57: 171.
14. Homer J. Appl. Spectrosc. Rev. 1975; 9: 1.
15. Kuchel PW, Chapman BE, Bubb WA, Hansen PE, Durrant CJ, Hertzberg MP. Concepts Magn. Reson. Part A 2003; 18A: 56.
16. Exner O. In Correlation Analysis of Chemical Data. Plenum Press: New York, 1988.
17. Smith GW. In Handbook of Chemistry and Physics, Weast RC (ed.). The Chemical Rubber Co.: Cleveland, OH, 1971; E114.
18. Frei K, Bernstein HJ. J. Chem. Phys. 1962; 37: 1891.
19. Durrant CJ, Hertzberg MP, Kuchel PW. Concepts Magn. Reson. Part A 2003; 18A: 72.
20. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji M, 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 JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03, Revision C.02. Gaussian, Inc.: Wallingford, CT, 2004.
21. Becke AD. J. Chem. Phys. 1993; 98: 5648.
22. Lee C, Yang W, Parr RG. Phys. Rev. 1988; B37: 785.
23. Ditchfield R. Mol. Phys. 1974; 27: 789.
24. Wolinski K, Hilton JF, Pulay P. J. Am. Chem. Soc. 1990; 112: 8251.
25. Dransfeld A. Chem. Phys. 2004; 298: 47.
26. Afonin AV, Ushakov IA, Sobenina LN, Stepanova ZV, Petrova OV, Trofimov BA. Magn. Reson. Chem. 2006; 44: 59.
27. Ruden T, Ruud K. In Calculation of NMR and EPR Parameters. Theory and Applications, Kaupp M, Bühl M, Malkin VG (eds). Wiley-VCH: Weinheim, 2004; 172.
28. Exner O, Böhm S. J. Magn. Reson. 2004; 25: 1975.
29. Kaupp M. In Calculation of NMR and EPR Parameters. Theory and Applications, Kaupp M, Bühl M, Malkin VG (eds). Wiley-VCH: Weinheim, 2004; 305.
30. Taft RW, Price E, Fox IR, Lewis IC, Andersen KK, Davis GT. J. Am. Chem. Soc. 1963; 85: 709.
31. Taft RW, Price E, Fox IR, Lewis IC, Andersen KK, Davis GT. J. Am. Chem. Soc. 1963; 85: 3146.
32. Reynolds WF, Gomes A, Maron A, Macintyre DW, Tanin A, Hamer GK, Peat IR. Can. J. Chem. 1983; 61: 2376.
33. Cook IB, Sadek M, Ternai B. Aust. J. Chem. 1989; 42: 259.
34. Böhm S, Paoík P, Exner O. New J. Chem. 2006; 30: 384.
35. Charton M. Prog. Phys. Org. Chem. 1981; 13: 119.
36. Buděšínský M, Exner O. Magn. Reson. Chem. 1989; 27: 585.
37. Dawson DA, Reynolds WF. Can. J. Chem. 1975; 53: 373.
38. Olah GA, Iyer PS, Prakash GKS, Krishnamurthy VV. J. Am. Chem. Soc. 1984; 106: 7073.
39. Exner O, Buděšínský M. Collect. Czech. Chem. Commun. 1992; 57: 497.
40. Inamoto N, Masuda S, Takumaru T, Tori K, Yoshida M, Yoshimura Y. Tetrahedron Lett. 1976; 3707.
41. Bromilow J, Brownlee RTC, Craik DJ. Aust. J. Chem. 1977; 30: 351.
42. Exner O, Dahn H, Péchy P. Magn. Reson. Chem. 1992; 30: 381.
43. Exner O, Buděšínský M. Collect. Czech. Chem. Commun. 1991; 56: 2234.
44. Marcus SH, Reynolds WP, Miller SI. J. Org. Chem. 1966; 31: 1872.
45. Fraser RR, Gurudata X, Reyes-Zamora C, Swingle RB. Can. J. Chem. 1968; 46: 1595.
46. Yokoyama T, Wiley GR, Miller SI. J. Org. Chem. 1969; 34: 1859.
47. Shorter J. In Advances in Linear Free Energy Relationships, Chapman NB, Shorter J (eds). Plenum Press: London, 1972; 71.
48. Böhm S, Fiedler P, Exner O. New J. Chem. 2004; 28: 67.