Molecular Complexes of p-Chloranil with Aniline, Phenol and their Derivatives

Abstract:

Classification of simple supramolecular structures (for example molecular complexes), which has been introduced and described by Mulliken [1], is based on types of molecular orbitals of the components. In the paper [2], disadvantages of such classification are shown, which motivate us to return to the re-examination properties of molecular complexes. By this reason, there is a need to research the molecular complexes of one electron acceptor with a wide range of electron donor molecules. This paper have continued work (Part I [3]) on the chloranil complexes by studying the spectral properties complexes of N- and O-unsubstituting anilines and phenols. The present work aimed at analyzing linear relation the energies of charge-transfer bands of molecular complexes are related to ionization potentials of the donor components. All complexes conform to linear relations like involving both adiabatic and vertical ionization potentials of donor components. Mulliken [1] has been proposed to apply the vertical ionization potentials of donor components only. The development of photoelectron spectroscopy has led to the measurement of adiabatic and vertical ionization energies for thousands of molecules, which allow theirs to the present analysis of spectral properties molecular complexes.

• Periodical: Key Engineering Materials (Volume 670)
• Pages: 89-94
• DOI: https://doi.org/10.4028/www.scientific.net/KEM.670.89
• Online since: October 2015
• Authors: Boris Pryalkin, Yulia S. Bodagova
• Keywords: Aniline, Charge-Transfer Complexes, Electron Spectroscopy, Molecular Complexes, P-Chloranil, Phenol, п-

References

[1] R.S. Mulliken, and W.B. Person, Molecular Complexes, New York: Wiley, (1969).

[2] B.S. Pryalkin, Molecular Complexes of 1, 3, 5-Trinitrobenzene with Naphthalene and Its Derivatives, Russ, J. Gen. Chem., 79 (2009) 2359-2366.

DOI: 10.1134/s1070363209110139

[3] B.S. Pryalkin, Molecular Complexes of Quinones: I. π–π Complexes of p-Chloranil with Benzene and Its Derivatives, Russ. J. Gen. Chem., 83 (2013) 303-310.

DOI: 10.1134/s1070363213020126

[4] E.N. Guryanova, I.P. Goldshtein, I.P. Romm, The Donor–Acceptor Bond Moscow, Chemistry (Moskva, Khimiya - in Russian), (1973).

[5] V.I. Vovna, Electronic Structure of Organic Compounds according to the Data of Photoelectron Spectroscopy Moscow: Science (Moskva: Nauka - in Russian), (1991).

[6] Dissociation Energies of Chemical Bonds. Ionization Potentials and Electron Affinities Moscow: Science (Moskva: Nauka - in Russian), (1974).

[7] V.I. Vovna, F.I. Vilesov, Photoelectron spectroscopy of free molecules: Structure and interaction of molecular orbitals, Success of photonic (Uspekhi fotoniki – in Russian), 5 (1973) 3-149.

[8] W.R. Carper, Charge-transfer complexes and donor molecule properties chloranil-aniline complexes, J. Phys. Chem., 69 (1966) 1707-1710.

DOI: 10.1021/j100889a044

[9] P.C. Dwivedi, Spectroscopic studies of the electron donor-acceptor interaction between chloranil and anilines, Curr. Sci., 51 (1982) 1152-1153.

[10] L.V. Koshkin, T.P. Filippova, The spectral properties of complexes aromatic amines with quinones are related to antioxydation function of amine compounds, Proc. Hig. Educ. Inst. Ser. Chem. Chem. Technol. (Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol. - in Russian), 33 (1990).

DOI: 10.6060/ivkkt.20236607

[11] B. Prabitha, S. Periandy, K. Govindan, Spectrophotometric studies of charge transfer complexes between p-chloranil and certain aromatic amines at 302 K, Asian J. Chem., 11 (1999) 1205-1210.

[12] P.H. Gore, B.B. Wheals, A spectrophotometric study of the colour reaction between chloranil and aromatic amines, Anal. chim. acta., 30 (1964) 34-39.

DOI: 10.1016/s0003-2670(00)88681-x

[13] Dulal Chandra Mukherjee, Asish Kumar Chandra, Molecular Complexes of Anilines with Chloranil, J. Phys. Chem., 68 (1964) 477-480.

DOI: 10.1021/j100785a007

[14] Xingwei Guo, H. Mayr. Quantification of the Ambident Electrophilicities of Halogen-Substituted Quinones. J. Amer. Chem. Soc. 136 (2014) 11499-11512.

DOI: 10.1021/ja505613b

[15] L.V. Koshkin, N.N. Rzhevskaya, I.M. Rodionova, O.P. Yablonskiij, Electron and proton donor properties of phenols on course formation of charge transfer complexes with chloranil and formation of H-complexes with dioxane, J. Phys. Chem. (Zh. Fiz. Khim. - in Russian), 59 (1985).

[16] B.F. Malichenko, Molecular diagrams of organic compounds: Reference book, Kiev, Naukova Dumka (Kiev, Naukova Dumka - in Russian), (1982).

[17] A.F. Pozharskij, Conception of π-superfluous in chemistry of heteroaromatic compounds, Chem. Heterocycl. Comp. (Chim. Geteroziklich. Soedin. - in Russian), (1977) 723-740.

[18] V.E. Sahini, L. Tellea, CNDO/2 calculation of anizidine isomers, Rev. roum. chim., 26 (1981) 3-7.

[19] B.S. Pryalkin, Molecular Complexes of 1, 3, 5-Trinitrobenzene, J. Gen. Chem. USSR (Engl. Transl. ), 52 (1982) 128-135.

[20] F.H. Herbstein. Crystalline molecular complexes and compounds: Structure and Principles, Oxford: Oxford University Press, (2005).