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Volumn 72, Issue 20, 2007, Pages 7587-7596

Orientational effect of aryl groups in aryl selenides: How can 1H and 13C NMR chemical shifts clarify the effect?

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SHIFT; EQUILIBRIUM CONSTANTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY; SOLUTIONS;

EID: 34848817967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070988g     Document Type: Article
Times cited : (20)

References (44)
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    • Patai, S, Rappoport, Z, Eds, John-Wiley and Sons: New York, Vols, and 2
    • The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; John-Wiley and Sons: New York, 1986; Vols. 1 and 2.
    • (1986) The Chemistry of Organic Selenium and Tellurium Compounds , vol.1
  • 3
    • 0003987564 scopus 로고
    • Liotta, D, Ed, Wiley-Interscience: New York
    • Organic Selenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987.
    • (1987) Organic Selenium Chemistry
  • 8
    • 34848918675 scopus 로고
    • Patai, S, Rappoport, Z, Eds, John-Wiley and Sons: New York, Chapter 6
    • (c) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; John-Wiley and Sons: New York, 1986; Vol. 1, Chapter 6.
    • (1986) The Chemistry of Organic Selenium and Tellurium Compounds , vol.1
  • 9
    • 0004060681 scopus 로고    scopus 로고
    • Klapotke, T. M, Broschag, M, Eds; Wiley: New York
    • 77Se NMR Chemical Shifts; Klapotke, T. M., Broschag, M., Eds; Wiley: New York, 1996.
    • (1996) 77Se NMR Chemical Shifts
  • 22
    • 34250876876 scopus 로고    scopus 로고
    • Chem. Eur. J. 2007, 13, 5282-5293.
    • (2007) Eur. J , vol.13 , pp. 5282-5293
    • Chem1
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    • 22
    • 22
  • 25
    • 34848817842 scopus 로고    scopus 로고
    • The importance of relative conformations in the substituent effects between substituents and probe sites is pointed out. See, for example: Bordwen, K.; Grubbs, E. J. Angular Dependence of Dipolar Substituent Effects. In Progress in Physical Organic Chemistry; Taft, R. W., Ed.; John Wiley & Sons: New York, 1993; 19, pp 183-224. See also refs cited therein.
    • The importance of relative conformations in the substituent effects between substituents and probe sites is pointed out. See, for example: Bordwen, K.; Grubbs, E. J. Angular Dependence of Dipolar Substituent Effects. In Progress in Physical Organic Chemistry; Taft, R. W., Ed.; John Wiley & Sons: New York, 1993; Vol. 19, pp 183-224. See also refs cited therein.
  • 26
    • 84986617286 scopus 로고    scopus 로고
    • A basic set containing substituents of differing relative polar and resonance effects has been suggested: two from NMe2, OMe, NH 2, two halogens but not both Cl and Br, Me, H, and two electron-withdrawing groups. From a spectroscopic point of view, to avoid any specific interactions, any d-orbitals, or any mass effect, the following substituents are recommended: Y, NMe2, OMe, F, Cl, Me, H, and two from CF3, CN, COY, and NO2. See: Topsom, R. D. The Nature and Analysis of Substituent Electronic Effects. In Progress in Physical Organic Chemistry; Taft, R. W, Ed, John Wiley & Sons; New York, 1976; 12, pp 1-20
    • 2. See: Topsom, R. D. The Nature and Analysis of Substituent Electronic Effects. In Progress in Physical Organic Chemistry; Taft, R. W., Ed.; John Wiley & Sons; New York, 1976; Vol. 12, pp 1-20.
  • 27
    • 34848822372 scopus 로고    scopus 로고
    • 3 solutions were used for NMR measurements. The concentrations would be lower for the compounds of low solubility, such as 1j and 2j, especially at 213 K. However, the concentration dependence of δ(H) and δ(C) of 1 and 2 is usually small when they are less than 0.050 M.
    • 3 solutions were used for NMR measurements. The concentrations would be lower for the compounds of low solubility, such as 1j and 2j, especially at 213 K. However, the concentration dependence of δ(H) and δ(C) of 1 and 2 is usually small when they are less than 0.050 M.
  • 31
    • 34848884086 scopus 로고    scopus 로고
    • Frisch, M. J. et al. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford CT, 2004.
    • Frisch, M. J. et al. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford CT, 2004.
  • 32
    • 34848829011 scopus 로고    scopus 로고
    • Glendening, E. D, Reed, A. E, Carpenter, J. E, Weinhold, F. NBO, version 3.1
    • Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO, version 3.1.
  • 33
    • 34848871133 scopus 로고    scopus 로고
    • The deviation of the data for Y = a is often observed in such plots; however, the reason is not clear.
    • The deviation of the data for Y = a is often observed in such plots; however, the reason is not clear.
  • 34
    • 34848837182 scopus 로고    scopus 로고
    • SCS, which must be responsible for the poor correlation.
    • SCS, which must be responsible for the poor correlation.
  • 35
    • 34848829649 scopus 로고    scopus 로고
    • SCS is also analyzed as two correlations: y = 1.300x -7.538 (r = 0.9999) for Y = b, c, and e, and y = 0.901x -3.831 (r = 0.999) for Y = d, f-j, although data for Y = a deviate the line.
    • SCS is also analyzed as two correlations: y = 1.300x -7.538 (r = 0.9999) for Y = b, c, and e, and y = 0.901x -3.831 (r = 0.999) for Y = d, f-j, although data for Y = a deviate the line.
  • 39
    • 0037439843 scopus 로고    scopus 로고
    • The contribution of relativistic terms has been pointed out for heavier atoms, but the perturbation would be small for the selenium nucleus. See
    • The contribution of relativistic terms has been pointed out for heavier atoms, but the perturbation would be small for the selenium nucleus. See: Fukuda, R.; Hada, M.; Nakatsuji, H. J. Chem. Phys. 2003, 118, 1015-1026.
    • (2003) J. Chem. Phys , vol.118 , pp. 1015-1026
    • Fukuda, R.1    Hada, M.2    Nakatsuji, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.