A GIAO/DFT study of 1H, 13C and 15N shieldings in amines and its relevance in conformational analysis

Magnetic Resonance in Chemistry

Volumn 42, Issue 11, 2004, Pages 955-961

  Alkorta, Ibon ^a   Elguero, José ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Amines; DFT; GIAO; Lone pair

Indexed keywords

AMINES; CONFORMATIONS;

ANISOTROPY EFFECT; B3LYP/6-311++G; CONFORMATIONAL ANALYSIS; DFT; DFT STUDY; ETHYLAMINE; GIAO; GIAO DFT; LONE PAIR;

SHIELDING;

AMINE;

ANISOTROPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CORRELATION ANALYSIS; DATA ANALYSIS; DENSITY FUNCTIONAL THEORY; MATHEMATICAL COMPUTING; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 10944255829     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1460     Document Type: Article

References (48)

1. Sebag AB, Forsyth DA, Plante MA. J. Org. Chem. 2001; 66: 7967, and references cited therein.
2. Eliel EL, Wilen SH. Stereochemistry of Organic Compounds. Wiley: New York, 1994; 743.
3. Srinivasan PR, Lichter RL. J. Magn. Reson. 1977; 28: 227.
4. Berger S, Braun S, Kalinowski HO. NMR Spectroscopy of Non-Metallic Elements. Wiley: Chichester, 1997; 117.
5. Berger S, Braun S, Kalinowski HO. NMR Spectroscopy of Non-Metallic Elements. Wiley: Chichester, 1997; 118.
6. Liepin'sh EE, Trapentsier PT, Kalvin'sh IYa. Chem. Heterocycl. Compd. 1988; 1106.
7. 13C NMR Spectroscopy. Verlag Chemie: Weinheim, 1978; 178, 198.
8. Kalinowski HO, Berger S, Braun S. Carbon-13 NMR Spectroscopy. Wiley: Chichester, 1983; 222.
9. Chauvel JP, Folkend MM, True NS. Magn. Reson. Chem. 1987; 25: 101.
10. Carter RE, Drakenberg; T. J. Chem. Soc., Chem. Commun. 1972; 582.
11. Tafazzoli M, Suarez C, True NS, LeMaster CB, LeMaster CL. J. Phys. Chem. 1992; 96: 10 201.
12. Pretsch E, Clerc T, Seibl J, Simon W. Tablas para la Determinación Estructural par Métodot Espectroscópicos. Springer-Verlag Ibérica: Barcelona, 1998.
13. Dutler R, Rauk A, Sørensen TS. J. Am. Chem. Soc. 1987; 109: 3224.
14. Chadwick DJ. In Comprehensive Heterocyclic Chemistry, I, vol. 4, Katritsky AR, Rees CW (eds). Pergamon Press: Oxford, 1984; 170.
15. Abraham RJ, Nedforth CJ. Magn. Reson. Chem. 1988; 26: 334.
16. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
17. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
18. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
19. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
20. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
21. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
22. Alkorta I, Elguero J. Struct. Chem. 1998; 9: 187; Begtrup M, Balle R, Claramunt RM, Sanz D, Jiménez JA, Mó O, Yáñez M, Elguero J. THEOCHEM 1998; 453: 255; Claramunt RM, López C, Sanz D, Elguero J. Heterocycles 2001; 55: 2109; Jegerovic N, Jimeno ML, Alkorta I, Elguero J, Claramunt RM. Tetrahedron 2002; 58: 9089; Claramunt RM, López C, García MA, Denisov GS, Alkorta I, Elguero J. New J. Chem. 2003; 27: 734; Alkorta I, Elguero J. Struct. Chem. 2003; 14: 377; Dardonville C, Jimeno ML, Alkorta I, Elguero J. Org. Biomol. Chem. 2004; 2: 1587.
23. Kalinowski HO, Berger S, Braun S. Carbon-13 NMR Spectroscopy. Wiley: Chichester, 1988; 109.
24. Wehrli FW, Marchand AP, Wehrli S. Interpretation of Carbon-13 NMR Spectra. Wiley: Chichester, 1988; 52.
25. Emsley JW, Feeney J, Sutcliffe LH. High Resolution Nuclear Magnetic Resonance Spectroscopy. vol. 2, Pergamon Press: Oxford, 1966; 678; Karplus M. J. Chem. Phys. 1959; 30: 11; Karplus M. J. Phys. Chem. 1960; 64: 1793; Karplus M. J. Am. Chem. Soc. 1963; 85: 2870; Barfield M, Smith WB. J. Am. Chem. Soc. 1992; 114: 1574.
26. Emsley JW, Feeney J, Sutcliffe LH. High Resolution Nuclear Magnetic Resonance Spectroscopy. vol. 2, Pergamon Press: Oxford, 1966; 678; Karplus M. J. Chem. Phys. 1959; 30: 11; Karplus M. J. Phys. Chem. 1960; 64: 1793; Karplus M. J. Am. Chem. Soc. 1963; 85: 2870; Barfield M, Smith WB. J. Am. Chem. Soc. 1992; 114: 1574.
27. Emsley JW, Feeney J, Sutcliffe LH. High Resolution Nuclear Magnetic Resonance Spectroscopy. vol. 2, Pergamon Press: Oxford, 1966; 678; Karplus M. J. Chem. Phys. 1959; 30: 11; Karplus M. J. Phys. Chem. 1960; 64: 1793; Karplus M. J. Am. Chem. Soc. 1963; 85: 2870; Barfield M, Smith WB. J. Am. Chem. Soc. 1992; 114: 1574.
28. Emsley JW, Feeney J, Sutcliffe LH. High Resolution Nuclear Magnetic Resonance Spectroscopy. vol. 2, Pergamon Press: Oxford, 1966; 678; Karplus M. J. Chem. Phys. 1959; 30: 11; Karplus M. J. Phys. Chem. 1960; 64: 1793; Karplus M. J. Am. Chem. Soc. 1963; 85: 2870; Barfield M, Smith WB. J. Am. Chem. Soc. 1992; 114: 1574.
29. Emsley JW, Feeney J, Sutcliffe LH. High Resolution Nuclear Magnetic Resonance Spectroscopy. vol. 2, Pergamon Press: Oxford, 1966; 678; Karplus M. J. Chem. Phys. 1959; 30: 11; Karplus M. J. Phys. Chem. 1960; 64: 1793; Karplus M. J. Am. Chem. Soc. 1963; 85: 2870; Barfield M, Smith WB. J. Am. Chem. Soc. 1992; 114: 1574.
30. Günther H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry (2nd edn). Wiley: Chichester, 1995; 78; McConnell HM. J. Chem. Phys. 1957; 27: 226; Martin NH, Allen NW, Minga EK, Ingrassia ST, Brown JD, J. Am. Chem. Soc. 1998; 120: 11 510; Elguero J, Alkorta I. New J. Chem. 1998; 22: 381.
31. Günther H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry (2nd edn). Wiley: Chichester, 1995; 78; McConnell HM. J. Chem. Phys. 1957; 27: 226; Martin NH, Allen NW, Minga EK, Ingrassia ST, Brown JD, J. Am. Chem. Soc. 1998; 120: 11 510; Elguero J, Alkorta I. New J. Chem. 1998; 22: 381.
32. Günther H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry (2nd edn). Wiley: Chichester, 1995; 78; McConnell HM. J. Chem. Phys. 1957; 27: 226; Martin NH, Allen NW, Minga EK, Ingrassia ST, Brown JD, J. Am. Chem. Soc. 1998; 120: 11 510; Elguero J, Alkorta I. New J. Chem. 1998; 22: 381.
33. Günther H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry (2nd edn). Wiley: Chichester, 1995; 78; McConnell HM. J. Chem. Phys. 1957; 27: 226; Martin NH, Allen NW, Minga EK, Ingrassia ST, Brown JD, J. Am. Chem. Soc. 1998; 120: 11 510; Elguero J, Alkorta I. New J. Chem. 1998; 22: 381.
34. ApSimon JW, Elguero J, Fruchier A, Mathieu D, Phan Tan Luu R. Can. J. Chem. 1974; 52: 2296.
35. Brois SJ. J. Am. Chem. Soc. 1967; 89: 4242.
36. Breuer E, Melumad D. J. Org. Chem. 1973; 38: 1601.
37. Martino R, Abeba J, Lattes, A. J. Heterocycl. Chem. 1973; 10: 91.
38. Crabb TA, Katritzky AR. Adv. Heterocycl. Chem. 1984; 36: 1.
39. Brois SJ. J. Am. Chem. Soc. 1967; 89: 4242.
40. Lambert JB, Oliver WL, Packard BS. J. Am. Chem. Soc. 1971; 93: 933.
41. Drakenberg T, Lehn JM. J. Chem. Soc., Perkin Trans. 2 1972; 532.
42. Becke AD. J. Chem. Phys. 1993; 98: 5648; Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785.
43. Becke AD. J. Chem. Phys. 1993; 98: 5648; Lee C, Yang W, Parr RG. Phys. Rev. B 1988; 37: 785.
44. Frisch MJ, Pople JA, Krishnam R, Binkley JS. J. Chem. Phys. 1984; 80: 3265.
45. Ditchfield R. Mol. Phys., 1974; 27: 789; Dodds JL, McWeeny R, Sadlej AJ. Mol. Phys. 1980; 41: 1419.
46. Ditchfield R. Mol. Phys., 1974; 27: 789; Dodds JL, McWeeny R, Sadlej AJ. Mol. Phys. 1980; 41: 1419.
47. Bader RFW. Atoms in Molecules. A Quantum Theory. Oxford University: New York, 1990.
48. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen W, Wong MW, Andres JL, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98. Gaussian: Pittsburgh, PA, 1998.