Unexpected chirality in trans-1,4-dicyanocyclohexane
The experimental non-zero dipole moment of trans-1,4-dicyanocyclohexane was verified through a procedure little sensitive to solute/solvent interactions. This value cannot be explained on the basis of the generally accepted centrosymmetry for trans-1,4-derivatives of cyclohexane. NMR data of both th...
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1988
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 05830caa a22006617a 4500 | ||
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| 001 | PAPER-810 | ||
| 003 | AR-BaUEN | ||
| 005 | 20241115133558.0 | ||
| 008 | 190411s1988 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-45449121752 | |
| 030 | |a JMOSB | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Barón, Máximo | |
| 245 | 1 | 0 | |a Unexpected chirality in trans-1,4-dicyanocyclohexane |
| 260 | |c 1988 | ||
| 270 | 1 | 0 | |m Barón, M.; Departamento de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 1- Ciudad Universitaria-Nunez, 1428 Buenos Aires, Argentina |
| 504 | |a Barón, de Zenobi, Davidson, (1975) J. Mol. Struct., 24, p. 432 | ||
| 504 | |a Herst Müller, Influence of the solvent on dipole-moments (1934) Transactions of the Faraday Society, 30, p. 729 | ||
| 504 | |a Pijpers, (1958) Thesis, , University of Leyden | ||
| 504 | |a Barón, Buep, (1982) An. Asoc. Quím. Argent., 70, p. 571 | ||
| 504 | |a Aihara, Kitazawa, Iwasaki, Dipole Moment, Molecular Conformation and Crystal Structure of 1,4-Bis(dicyanomethylene)cyclohexane (1968) Bulletin of the Chemical Society of Japan, 41 (4), p. 1034 | ||
| 504 | |a Kozima, Yoshimo, Molecular Structures of trans-1,4-Dihalogenocyclohexanes (1953) Journal of the American Chemical Society, 57, p. 166 | ||
| 504 | |a Woldback, Nielsen, Klaboe, The conformation and vibrational spectra of trans-1,4-dihalocyclohexanes (1980) Journal of Molecular Structure, 66, p. 31 | ||
| 504 | |a Barón, Vapor-phase dipole moment values from solution measurements (1985) The Journal of Physical Chemistry, 89, pp. 4873-4875 | ||
| 504 | |a M. Barón and E. Sánchez Arevalo, J. Chem. Educ., in press; Leitch, Gagnon, Cambron, (1950) Can. J. Chem., 28 B, p. 256 | ||
| 504 | |a Honer, Meyer, Versuche zum Vorgang der Wasserstoffübertragung, X. Der H-D-Austausch Zwischen Deuterium-Gas und Alkylbenzolen in Gegenwart von Raney-Nickel (1964) Justus Liebigs Annalen der Chemie, 680, p. 1 | ||
| 504 | |a Larnaudie, Isomérie des dérivés monosubstitués du cyclohexane (1954) Journal de Physique et le Radium, 15, p. 650 | ||
| 504 | |a Horntredt, Klaboe, Conformational Spectroscopic Studies of Cyano- and Isocyanatocyclohexane. (1975) Acta Chemica Scandinavica, 29 A, p. 528 | ||
| 504 | |a Wiberg, Walters, Dailey, (1985) J. Am. Chem. Soc., 107 (17), p. 4860. , and refs. cited therein | ||
| 504 | |a Horndtredt, Klaboe, Conformational Spectroscopic Studies of Cyano- and Isocyanatocyclohexane. (1975) Acta Chemica Scandinavica, 29 A, p. 528 | ||
| 504 | |a Allinger, Szkrybalo, (1962) J. Org. Chem., 27, p. 4603 | ||
| 504 | |a Hendrickson, (1961) J. Am. Chem. Soc., 83, p. 4537 | ||
| 504 | |a Dewar, Thiel, (1977) J. Am. Chem. Soc., 99, p. 4899 | ||
| 504 | |a Jensen, Hackett Bushweller, Beck, (1969) J. Am. Chem. Soc., 91, p. 344 | ||
| 504 | |a Hawkes, Utley, (1969) J. Chem. Soc., p. 1033. , Chem. Commun | ||
| 504 | |a Grant, Hirst, (1963) J. Chem. Phys., 38 (2), p. 470 | ||
| 504 | |a Tables of Interatomci Distances (1958) Special Publications 11 and 18, p. 1965. , The Chemical Society, London | ||
| 504 | |a Bastiansen, Fernholt, Seip, Kambara, Kuchitsu, (1983) J. Mol. Struct., 18, p. 163 | ||
| 504 | |a Mislow, Siegel, (1984) J. Am. Chem. Soc., 106, p. 3319 | ||
| 504 | |a Huber, Wright, THE ELECTRICAL POLARIZATION OF 1,4-BENZOQUINONE AND RELATED SUBSTANCES (1964) Canadian Journal of Chemistry, 42, p. 1446 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a The experimental non-zero dipole moment of trans-1,4-dicyanocyclohexane was verified through a procedure little sensitive to solute/solvent interactions. This value cannot be explained on the basis of the generally accepted centrosymmetry for trans-1,4-derivatives of cyclohexane. NMR data of both this compound and its C-1, C-4 di-deuteroderivative, as well as semi-empirical theoretical calculations with the MNDO methods show that besides a centro-symmetric form there are also low energy stable non-centrosymmetric geometries. The latter exist as a helical deformation that can account for the non-zero value of the experimental dipole moment. © 1988. |l eng | |
| 536 | |a Detalles de la financiación: University of Salford Manchester | ||
| 536 | |a Detalles de la financiación: of the Carrera de1 Investigador. Fellow, Consejo National de Investigaciones Cientificas y TBcnicas. | ||
| 536 | |a Detalles de la financiación: The authors are indebted to the Consejo National de Investigaciones Cientificas y TCcnicas for continued support of their work and express their gratitude to Professors John A. Ladd (Salford University, Ct. Britain) and Valdemar J. Kowalewski (this Department) for their assistance with the NMR spectra. | ||
| 593 | |a Departamento de Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 1- Ciudad Universitaria-Nunez, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a Medrano, J.A. | |
| 700 | 1 | |a Ferraro, M. | |
| 700 | 1 | |a Buep, Adrián Hugo | |
| 773 | 0 | |d 1988 |g v. 172 |h pp. 355-367 |k n. C |p J. Mol. Struct. |x 00222860 |w (AR-BaUEN)CENRE-222 |t Journal of Molecular Structure | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-45449121752&doi=10.1016%2f0022-2860%2888%2987028-5&partnerID=40&md5=f3d301fbf92b9a333a8cd2861936a34d |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/0022-2860(88)87028-5 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00222860_v172_nC_p355_Baron |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00222860_v172_nC_p355_Baron |y Registro en la Biblioteca Digital |
| 961 | |a paper_00222860_v172_nC_p355_Baron |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 61763 | ||