Abstract
According to modern ideas about the configuration N,N-hydroxylamine and its derivatives nN(5a′)-nσ (2a″)-orbital are orthogonal [1], which reflects the character of nN- and nσ-electrons of vibration band contours. The replacement of the hydrogen atom by the methyl group pushes n-orbitals up to the values of the vertical ionization potentials 1.45 and 1.83 eV, leading to convergence of ОН-groups up to 0.47 eV [1–3]. Such significant changes in the electron configuration of the alkyl derivatives of hydroxylaminе should be expressed at the energies of the hydrogen bonds and the formed specific interactions and are supposed to be at higher energies of D–N•••H–N connections in H2N–OH in comparison with the realized specific interactions of D–N → CH3–N. As we mentioned earlier, that an insignificant reduction of the electron density at the nitrogen atom when replacing a hydrogen atom with the ethyl group was found using X-ray electron spectroscopy [4, 5].
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References
Rademacher P, Freckmann BJ (1980) Photoelektronenspektren und konformationsverhalten von hydroxylamin und methylhydroxylaminen. J Electron Spectrosc 19(3):251–259
Rademacher P, Freckmann B (1978) Photoelectron spectra and conformation of tetrahedron-1,2-oxasines and isozasines. Tetrahedron Lett 9:841–842
Nefedov VI, Vovna VI (1989) Electronic structure of organic and elementorganic compounds. Nauka, Moscow, p 199
Karlson TA (1981) Photoelectron and OZE- spectroscopy. Mech. Eng. Russia, Leningrad, p 431
Nefedov VI (1984) Infra red – spectroscopy of chemical compounds. Chemistry, Moscow
Chickos JS, Acree WE Jr (2002) Enthalpies of vaporization of organic and organometallic compounds, 1880–2002. J Phys Chem Rev Data 31:519–879
Gleiter R (1979) Photoelectron spectra and bonding in small ring hydrocarbons. Top Curr Chem 86:197–285
Honegger E, Yang ZZ, Hellbronner E et al (1985) Lone-pair ionization energies of diazabicycloalkanes. J Electron Spectrosc 36:297–304
Armstrong DR, Perkins PG (1969) Calculation σ – π and π – σ* – transfer at vinyl borium. J Chem Soc 7:1044
Kato H, Yamaguche K et al (1965) Electron structure some galogenides and alkyl borium and aluminum. Bull Chem Soc Japan 36:2144
Ehrenson S (1968) Theory of electron effect at formation of complex of trimethylamine with trimethylborium. Theor Chim Acta 10:193
Chickos JS, Acree WE Jr (2003) Enthalpies of sublimation of organic and organometallic compounds, 1910–2001. J Phys Chem Rev Data 32:537–698
Baev AK (1969) To problems of chemical nature of phase transformation. In: General and applied chemistry. Vysheischaia Educating, Minsk, pp 197–206
Baev AK (1969) Phase condition and complex formation ability of halogenide metals. In: General and applied chemistry, vol 1. Vysheischaia Educating, Minsk, pp 207–218
Vovna VI, Vilesov FI, Vovna VI, Vilesov FI (1974) Photoelectron specters and structure molecular orbital’s methylamines. Opt Spectrosc 34(2):436–438
Rao CNR, Basu PK, Hefre MS (1979) Systematic organic UV. Photoelectron spectroscopy. Appl Spectrosc Rev 15(1):1–193
Palmer MH, Moyes W, Spiers M, Ridyard JNF (1979) The electronic structure of substituted: benzenes: ab initio calculationsand photoelectron spectra for phenol, the methyl- and fluoro-derivatieves, and the dihydroxybenztnes. J Mol Struct 52(2):293–307
Debies TP, Rabalais JW (1972/1973) Photoelectron spectra of substituted benzenes: II. Seven valence electron substituents. J Electron Spectrosc 1(4):355–370
Palmer MH, Moyes W, Spiers M, Ridyard JNF (1979) The electronic structure of substituted: benztnes: a study of aniline, the toluidines, phenilentdiamines and fluoroaniline by photoelectrone spectroscopy and ab unitio calculations. J Mol Struct 53(2):235–249
Frost DC, Lau WN, McDowell CA, Westwood NPC (1982) A study by He I photoelectron spectroscopy of monomericnitrosomethane, the cis and trans dimmers and formaldoxime. J Phys Chem 86(18):3577–3581
Legon AC, Roberts BP, Wallwork FL (1990) Do methyl groups form hydrogen bonds? An answer from the rotational spectrum of ethane – hydrogen cyanide. Chem Phy Lett 191:97
Hobza P, Hovlas Z (2000) Blue-shifting hydrogen bodes. Chem Rev 100:4253
Yukhnevich GV, Tarakanova EG (1998) Hydrogen bond CH…O in liquid methanol. J Mol Struct 447:25
Ivanov EV, Puchovskie Yu P, Abrosimov VK (2004) About formation of weak hydrogen bonds CH•••O in liquid methanol. Abstract. IX international conference. The problem of solvation and complex formation in solutions, Plyos, p 345
Baev AK (2012) Specific intermolecular interactions of organic compounds. Springer, Heidelberg, p 434
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Baev, A.K. (2014). Specific Intermolecular Interactions of Amino Alcohols and Their Derivatives. In: Specific Intermolecular Interactions of Nitrogenated and Bioorganic Compounds. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-37472-2_8
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