15N NMR spectroscopy of 3-substituted 5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chlorides

Magnetic Resonance in Chemistry

Volumn 40, Issue 3, 2002, Pages 182-186

  Martins, Marcos A P ^a   Pereira, Claudio M P ^a   Sinhorin, Adilson P ^a   Rosa, Adriano ^a   Zimmermann, Nilo E K ^a   Bonacorso, Helio G ^a   Zanatta, Nilo ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

13C NMR; 15N NMR; Calculations; Chemical shifts; NMR; Pyrazolium chlorides; Substituent effects

Indexed keywords

BROMINE COMPOUNDS; CHLORINE COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

13C NMR; 15N NMR; MO CALCULATIONS; NMR DATA; NMR-SPECTROSCOPY; PYRAZOLIA CHLORIDE; SHIFT PARAMETERS; SUBSTITUENT EFFECT;

CHEMICAL SHIFT;

CHLORIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DATA ANALYSIS; MATHEMATICAL COMPUTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0036117424     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.987     Document Type: Article

References (42)

1. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
2. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
3. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
4. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
5. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
6. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
7. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
8. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
9. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
10. King MM, Yeh HJC, Dudek GO. Org. Magn Reson. 1976; 8: 208; Lippmaa E, Magi M, Novikov SS, Khmelnitski LL, Prihodko AS, Lebedev OV, Epishina LV. Org. Magn Reson. 1972; 4: 153; Duthaler RO, Roberts JD. J. Am. Chem. Soc. 1978; 100: 4969; Bachovchin WW, Roberts JD. J. Am. Chem. Soc. 1978; 100: 8041; Schuster LL, Roberts JD. J. Org. Chem. 1979; 44: 3864; Schuster LL, Cyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765; Hawkes GE, Randall EW, Elguero J, Marzin CJ. J. Chem. Soc. Perkin Trans. 21977; 1024; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1981; 11B: 1; Sohár P. Nuclear Magnetic Resonance Spectroscopy, vol. II. CRC Press: Boca Raton, FL, 1983; Witanowski M, Stefaniak L, Webb GA. Annu. Rep. NMR Spectrosc. 1986; 18: 1.
11. Chen BC, von Philipsborn W. Helv. Chim. Acta 1983; 66: 1537.
12. Cmoch P, Stefaniak L, Melzer E, Baloniak S, Webb GA. Magn. Resort. Chem. 1999; 37: 493.
13. Schuster II, Dyllick-Brenzinger C, Roberts JD. J. Org. Chem. 1979; 44: 1765.
14. Claramunt RM, Sanz D, Boyer G, Catalan J, de Paz JLG, Elguero J. Magn. Reson. Chem. 1993; 31; 791.
15. Yunfa L, Xu J, Yang Y, Wang K. Faming Zhuanli Shenping Gongkai Shuomingshu CN85-108315 A 13, 1987; Chem. Abstr. 109: 211043 1997; Ibánez M, Picó Y, Mañes J. J. Chromatogr. A 1996; 728: 325; 1998; 823: 137; 1996; 727: 245.
16. Yunfa L, Xu J, Yang Y, Wang K. Faming Zhuanli Shenping Gongkai Shuomingshu CN85-108315 A 13, 1987; Chem. Abstr. 109: 211043 1997; Ibánez M, Picó Y, Mañes J. J. Chromatogr. A 1996; 728: 325; 1998; 823: 137; 1996; 727: 245.
17. Yunfa L, Xu J, Yang Y, Wang K. Faming Zhuanli Shenping Gongkai Shuomingshu CN85-108315 A 13, 1987; Chem. Abstr. 109: 211043 1997; Ibánez M, Picó Y, Mañes J. J. Chromatogr. A 1996; 728: 325; 1998; 823: 137; 1996; 727: 245.
18. Yunfa L, Xu J, Yang Y, Wang K. Faming Zhuanli Shenping Gongkai Shuomingshu CN85-108315 A 13, 1987; Chem. Abstr. 109: 211043 1997; Ibánez M, Picó Y, Mañes J. J. Chromatogr. A 1996; 728: 325; 1998; 823: 137; 1996; 727: 245.
19. Yunfa L, Xu J, Yang Y, Wang K. Faming Zhuanli Shenping Gongkai Shuomingshu CN85-108315 A 13, 1987; Chem. Abstr. 109: 211043 1997; Ibánez M, Picó Y, Mañes J. J. Chromatogr. A 1996; 728: 325; 1998; 823: 137; 1996; 727: 245.
20. Stingelin W, Moser P. Ger. Offen. DE3544574 A1 1986; Chem. Abstr, 1997; 106: 6407; Fischer JC, Straley JM. Brit 1, 236, 656 (1971); Chem. Abstr. 1971; 75: 119 193; Enstschel R, Kaeppeli V. Ger. Offen. 2, 008, 784 (1970); Chem. Abstr. 1971; 74: 4650.
21. Stingelin W, Moser P. Ger. Offen. DE3544574 A1 1986; Chem. Abstr, 1997; 106: 6407; Fischer JC, Straley JM. Brit 1, 236, 656 (1971); Chem. Abstr. 1971; 75: 119 193; Enstschel R, Kaeppeli V. Ger. Offen. 2, 008, 784 (1970); Chem. Abstr. 1971; 74: 4650.
22. Stingelin W, Moser P. Ger. Offen. DE3544574 A1 1986; Chem. Abstr, 1997; 106: 6407; Fischer JC, Straley JM. Brit 1, 236, 656 (1971); Chem. Abstr. 1971; 75: 119 193; Enstschel R, Kaeppeli V. Ger. Offen. 2, 008, 784 (1970); Chem. Abstr. 1971; 74: 4650.
23. Stingelin W, Moser P. Ger. Offen. DE3544574 A1 1986; Chem. Abstr, 1997; 106: 6407; Fischer JC, Straley JM. Brit 1, 236, 656 (1971); Chem. Abstr. 1971; 75: 119 193; Enstschel R, Kaeppeli V. Ger. Offen. 2, 008, 784 (1970); Chem. Abstr. 1971; 74: 4650.
24. Stingelin W, Moser P. Ger. Offen. DE3544574 A1 1986; Chem. Abstr, 1997; 106: 6407; Fischer JC, Straley JM. Brit 1, 236, 656 (1971); Chem. Abstr. 1971; 75: 119 193; Enstschel R, Kaeppeli V. Ger. Offen. 2, 008, 784 (1970); Chem. Abstr. 1971; 74: 4650.
25. Stingelin W, Moser P. Ger. Offen. DE3544574 A1 1986; Chem. Abstr, 1997; 106: 6407; Fischer JC, Straley JM. Brit 1, 236, 656 (1971); Chem. Abstr. 1971; 75: 119 193; Enstschel R, Kaeppeli V. Ger. Offen. 2, 008, 784 (1970); Chem. Abstr. 1971; 74: 4650.
26. Cuadrado P, Nogal AM. Tetrahedron Lett. 1998; 39: 1449.
27. Martins MAP, Pereira CMP, Sinhorin AP, Bastos GP, Zimmermann NEK, Rosa A, Bonacorso HG, Zanatta N. Synth. Commun. 2002; 32: 419; Martins MAP, Colla A, Clar G, Fischer P, Krimmer S. Synthesis 1991; 6: 483; Martins MAP, Bastos GP, Bonacorso HG, Zanatta N, Siqueira GM, Flores AFC. Tetrahedron Lett. 1999; 40: 4309.
28. Martins MAP, Pereira CMP, Sinhorin AP, Bastos GP, Zimmermann NEK, Rosa A, Bonacorso HG, Zanatta N. Synth. Commun. 2002; 32: 419; Martins MAP, Colla A, Clar G, Fischer P, Krimmer S. Synthesis 1991; 6: 483; Martins MAP, Bastos GP, Bonacorso HG, Zanatta N, Siqueira GM, Flores AFC. Tetrahedron Lett. 1999; 40: 4309.
29. Martins MAP, Pereira CMP, Sinhorin AP, Bastos GP, Zimmermann NEK, Rosa A, Bonacorso HG, Zanatta N. Synth. Commun. 2002; 32: 419; Martins MAP, Colla A, Clar G, Fischer P, Krimmer S. Synthesis 1991; 6: 483; Martins MAP, Bastos GP, Bonacorso HG, Zanatta N, Siqueira GM, Flores AFC. Tetrahedron Lett. 1999; 40: 4309.
30. Kolehmainen E, Gawinecki R, Osmialowski B, Trzebiatowska K. Magn. Reson. Chem. 1997; 35: 778.
31. (a) Kolehmainen E, Lappalainen K, Saman D, Holy A, Günter J. Magn. Reson. Chem. 1998; 36: 442;
32. (b) Martin GE, Hadden CE. J. Nat. Prod. 2000; 63: 543;
33. (c) Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093.
34. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. J. Am. Chem. Soc. 1990; 107: 3902; Stewart JJP. In Reviews of Computational Chemistry, Lipkovitz K, Boyd DB (eds). VCH: New York, 1990.
35. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. J. Am. Chem. Soc. 1990; 107: 3902; Stewart JJP. In Reviews of Computational Chemistry, Lipkovitz K, Boyd DB (eds). VCH: New York, 1990.
36. HyperChem 6.03. Hypercube: Gainesville, FL, 1999.
37. Martins MAP, Zanatta N, Bonacorso HG, Siqueira GM, Flores AFC. Magn. Reson. Chem. 1999; 37: 852.
38. 17O NMR of Enol Ethers, vol. III, Atta-ur-Rahman (ed.). Harwood Academic Publishers: Amsterdam, in press.
39. 17O NMR of Enol Ethers, vol. III, Atta-ur-Rahman (ed.). Harwood Academic Publishers: Amsterdam, in press.
40. Levy GC (ed.). Topics in Carbon-13 NMR Spectroscopy, vol. 1. Wiley: New York, 1974; Wehrli EW, Wirthlin T. Interpretation of Carbon-13 NMR Spectra. Heyden: London, 1976; Grant DM, Paul EG. J. Am. Chem. Soc. 1964; 86: 2984.
41. Levy GC (ed.). Topics in Carbon-13 NMR Spectroscopy, vol. 1. Wiley: New York, 1974; Wehrli EW, Wirthlin T. Interpretation of Carbon-13 NMR Spectra. Heyden: London, 1976; Grant DM, Paul EG. J. Am. Chem. Soc. 1964; 86: 2984.
42. Levy GC (ed.). Topics in Carbon-13 NMR Spectroscopy, vol. 1. Wiley: New York, 1974; Wehrli EW, Wirthlin T. Interpretation of Carbon-13 NMR Spectra. Heyden: London, 1976; Grant DM, Paul EG. J. Am. Chem. Soc. 1964; 86: 2984.