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Volumn 29, Issue 5, 1996, Pages 229-234

Bent Bonds in Organic Compounds

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EID: 0000264260     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar950207a     Document Type: Article
Times cited : (213)

References (62)
  • 1
    • 0003577868 scopus 로고
    • Cornell University Press: Ithaca, NY
    • The deformation density is defined as the difference in electron density between the compound in question and that of a set of spherically symmetrical "proatoms" that are placed at the corresponding nuclear positions. It shows where electron density shifts in forming bonds: Dunitz, J. X-Ray Analysis and the Structures of Organic Compounds; Cornell University Press: Ithaca, NY, 1979.
    • (1979) X-Ray Analysis and the Structures of Organic Compounds
    • Dunitz, J.1
  • 5
    • 2542599804 scopus 로고
    • Beesley, R. M.; Thorpe, J. F. Proc. Chem. Soc. 1913, 29, 346. Beesley, R. M.; Thorpe, J. F. J. Chem. Soc. 1920, 117, 591.
    • (1920) J. Chem. Soc. , vol.117 , pp. 591
    • Beesley, R.M.1    Thorpe, J.F.2
  • 7
    • 84916810137 scopus 로고
    • Larson, H. O.; Woodward, R. B. Chem. Ind. 1959, 193. Larson, H. O. Ph.D. Thesis, Harvard, 1950. The letter from Beesley to Woodward is reproduced in this thesis.
    • (1959) Chem. Ind. , pp. 193
    • Larson, H.O.1    Woodward, R.B.2
  • 8
    • 85033741879 scopus 로고
    • Ph.D. Thesis, Harvard, The letter from Beesley to Woodward is reproduced in this thesis
    • Larson, H. O.; Woodward, R. B. Chem. Ind. 1959, 193. Larson, H. O. Ph.D. Thesis, Harvard, 1950. The letter from Beesley to Woodward is reproduced in this thesis.
    • (1950)
    • Larson, H.O.1
  • 9
    • 1842405085 scopus 로고
    • It is interesting to note that cyclopropanes are often prepared by elimination of HX (Schlatter, M. J. J. Am. Chem. Soc. 1941, 63, 1733), and that the first bicyclobutane derivative was prepared by this method (Wiberg, K. B.; Cuila, R. P. J. Am. Chem. Soc. 1959, 81, 5261). It is quite possible that a bicyclobutane could be prepared from the dibromo triester using appropriate reaction conditions, but this does not appear to have been examined.
    • (1941) J. Am. Chem. Soc. , vol.63 , pp. 1733
    • Schlatter, M.J.1
  • 10
    • 0001291047 scopus 로고
    • It is interesting to note that cyclopropanes are often prepared by elimination of HX (Schlatter, M. J. J. Am. Chem. Soc. 1941, 63, 1733), and that the first bicyclobutane derivative was prepared by this method (Wiberg, K. B.; Cuila, R. P. J. Am. Chem. Soc. 1959, 81, 5261). It is quite possible that a bicyclobutane could be prepared from the dibromo triester using appropriate reaction conditions, but this does not appear to have been examined.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 5261
    • Wiberg, K.B.1    Cuila, R.P.2
  • 14
    • 0010035344 scopus 로고
    • Coulson, C. A.; Moffitt, W. E. J. Chem. Phys. 1947, 15, 151. Philos. Mag. 1949, 40, 1.
    • (1949) Philos. Mag. , vol.40 , pp. 1
  • 16
    • 0001409247 scopus 로고
    • Chalerabartin, P.; Seiler, P.; Dunitz, J. D.; Schuler, A.-D.; Szeimies, G. J. Am. Chem. Soc. 1981, 103, 7378. Boese, R.; Meibach, T.; deMeijere, A. J. Am. Chem. Soc. 1991, 113, 1743.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1743
    • Boese, R.1    Meibach, T.2    DeMeijere, A.3
  • 19
    • 0003484549 scopus 로고
    • Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York
    • For a review on cyclopropylcarbinyl cations see: Wiberg, K. B.; Hess, B. A., Jr.; Ashe, A. J., III. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York, 1972; Vol. 3.
    • (1972) Carbonium Ions , vol.3
    • Wiberg, K.B.1    Hess Jr., B.A.2    Ashe III, A.J.3
  • 21
    • 0344257364 scopus 로고
    • Walsh, A. D. Nature 1947, 159, 167, 712. Trans. Faraday Soc. 1949, 45, 179.
    • (1947) Nature , vol.159 , pp. 167
    • Walsh, A.D.1
  • 22
    • 37049157774 scopus 로고
    • Walsh, A. D. Nature 1947, 159, 167, 712. Trans. Faraday Soc. 1949, 45, 179.
    • (1949) Trans. Faraday Soc. , vol.45 , pp. 179
  • 26
    • 1142296589 scopus 로고
    • The bond dissociation energies of cyclopropane and cyclobutane have not been measured. The values given are based on CBS-Q calculations that have been found to reproduce known C-H bond dissociation energies with an rms deviation of only ±1 kcal/mol: Ochterski, J.; Petersson, G.; Wiberg, K. B. J. Am. Chem. Soc. 1995, 117, 11299.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 11299
    • Ochterski, J.1    Petersson, G.2    Wiberg, K.B.3
  • 28
    • 0040469672 scopus 로고
    • Meiboom, S.; Snyder, L. C. J. Chem. Phys. 1970, 52, 3857. Wright, J. S.; Salem, L. J. Chem. Soc., Chem. Commun. 1969, 1370.
    • (1970) J. Chem. Phys. , vol.52 , pp. 3857
    • Meiboom, S.1    Snyder, L.C.2
  • 35
    • 0008810694 scopus 로고
    • Palke, W. E. J. Am. Chem. Soc. 1986, 108, 6543. Schulz, P. A.; Messmer, R. P. J. Am. Chem. Soc. 1993, 115, 10925, 10938.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6543
    • Palke, W.E.1
  • 39
    • 0001185436 scopus 로고
    • Decius, J. C. J. Mol. Spectrosc. 1975, 57, 348. Decius, J. C.; Mast, G. B. J. Mol. Spectrosc. 1978, 70, 294. Mast, G. B.; Decius, J. C. J. Mol. Spectrosc. 1980, 79, 158.
    • (1975) J. Mol. Spectrosc. , vol.57 , pp. 348
    • Decius, J.C.1
  • 40
    • 0344111598 scopus 로고
    • Decius, J. C. J. Mol. Spectrosc. 1975, 57, 348. Decius, J. C.; Mast, G. B. J. Mol. Spectrosc. 1978, 70, 294. Mast, G. B.; Decius, J. C. J. Mol. Spectrosc. 1980, 79, 158.
    • (1978) J. Mol. Spectrosc. , vol.70 , pp. 294
    • Decius, J.C.1    Mast, G.B.2
  • 41
    • 0004446575 scopus 로고
    • Decius, J. C. J. Mol. Spectrosc. 1975, 57, 348. Decius, J. C.; Mast, G. B. J. Mol. Spectrosc. 1978, 70, 294. Mast, G. B.; Decius, J. C. J. Mol. Spectrosc. 1980, 79, 158.
    • (1980) J. Mol. Spectrosc. , vol.79 , pp. 158
    • Mast, G.B.1    Decius, J.C.2
  • 42
    • 0001878056 scopus 로고
    • Nakatsuji, H. J. Am. Chem. Soc. 1974, 96, 24. Figeya, H. P.; Berckmans, D.; Geerlings, P. J. Mol. Struct. 1979, 57, 271.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 24
    • Nakatsuji, H.1
  • 45
    • 34250727254 scopus 로고
    • For a comparison of the charges calculated via a variety of methods, cf. Wiberg, K. B.; Rablen, P. R. J. Comput. Chem. 1993, 14, 1504.
    • (1993) J. Comput. Chem. , vol.14 , pp. 1504
    • Wiberg, K.B.1    Rablen, P.R.2
  • 48
  • 50
  • 51
    • 0004592759 scopus 로고
    • Wiberg, K. B.; Waldron, R. F.; Schulte, G.; Saunders, M. J. Am. Chem. Soc. 1991, 113, 971. Hydrogen bonds of this type have also been found in other cases: Cf. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747.
    • (1995) J. Phys. Chem. , vol.99 , pp. 9747
    • Koch, U.1    Popelier, P.L.A.2
  • 56
    • 33947478901 scopus 로고
    • Cf. Gillespie, R. J. J. Chem. Educ. 1963, 40, 295; 1970, 47, 18.
    • (1970) J. Chem. Educ. , vol.47 , pp. 18
  • 58
    • 49649142387 scopus 로고
    • and references therein
    • Tanabe, K. Spectrochim. Acta 1972, A28, 407 and references therein.
    • (1972) Spectrochim. Acta , vol.A28 , pp. 407
    • Tanabe, K.1


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