Abstract
The frequencies and intensities of the two tautomeric structures of the N,\(N'\)-diphenylguanidine monomer and its hydrogen-bonded cyclic dimers were calculated for structure elucidation of the monomer and dimer forms of this compound and identification of the stretching vibration band νNH of this molecule in solution. Ab initio HF/3-21G and B3LYP/6-31G(d,p) calculations of DPG monomers and cyclic associates suggest that the asymmetric tautomer is dominant, proving that the dimer structures with two C=(Ph)N...H–NPh hydrogen bonds prevail in solution. An assignment of IR absorption frequencies of DPG in solution is suggested.
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REFERENCES
S. Patai and Z. Rappoport (eds.), The Chemistry of Amidines and Imidates, Wiley, Chichester (1991).
J. V. Greehill and P, Lue, in: Progress in Medicinal Chemistry, Vol. 30, G. P. Ellis and D. K. Luscombe (eds.), Elsevier, Amsterdam (1993), p. 203.
N. L. Reddy, L.-Y. Hu, R. E. Cotter, et al., J. Med. Chem., 37, 260–267 (1994).
A. Koll, M. Rospenk, S. F. Bureiko, and V. N. Bocharov, J. Phys. Org. Chem., 9, 487–497 (1996).
S. F. Bureiko, V. N. Bocharov, A. Koll, and M. Rospenk, Zh. Strukt. Khim., 39, 618–625 (1998).
L. N. Zakharov, V. G. Andrianov, and Yu. T. Struchkov, Kristallografiya, 25, 65–70 (1980).
G. Alagona, C. Chio, P. I. Nagy, and G. J. Durant, J. Phys. Chem., 98, 5422–5430 (1994).
B. Clement and T. Kamchen, Chem. Ber., 119, 1101–1104 (1986).
S. F. Bureiko and I. V. Chernyshova, J. Mol. Struct., 263, 37–44 (1991).
S. F. Bureiko and I. V. Chernyshova, Zh. Fiz. Khim., 63, 319–322 (1993).
GRAMS, Galactic Inc., Salem, NH (1997).
V. E. Borisenko and A. V. Morev, J. Mol. Struct., 322, 309–320 (1994).
M. Rutkis and I. Eidus, Izv. Latv. Akad. Nauk, Ser. Khim., No. 4, 447–454 (1988).
M. J. Frish, G. W. Trucks, H. B. Schlegel, et al., GAUSSIAN-94, Revision E.2, Gaussian Inc., Pittsburg PA (1995).
J. K. Labanowski and J. W. Andzelm, Density Functional Methods in Chemistry, Springer, New York (1991).
A. D. Becke, J. Chem. Phys., 98, 5648–5652 (1993).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785–797 (1988).
A. D. Becke, Phys. Rev. A, 38, 3098–3109 (1988).
A. Filarowski and A. Koll, Vibr. Spectr., 12, 15–24 (1996).
X. Jimei, G. Xuedong, C. Yingnan, and X. Heming, J. Mol. Struct. (Theochem), 489, 151–156 (1999).
J. A. Pople, R. Schlegel, R. Krishnan, et al., Int. J. Quant. Chem., 15, 269–282 (1981).
M. Karni, I. Oref, S. Barzilai-Gilloa, and A. Lifshitz, J. Phys. Chem., 92, 6924–6929 (1988).
M. Przeslawska, Praca doctorska, University Publishers, Wroclaw (1999).
J. J. P. Steward, J. Comput. Chem., 10, 221–264 (1989).
A. Karpfen, C. M. Choi, and M. Kertesz, J. Phys. Chem., 101, 7026–7433 (1997).
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Bureiko, S.F., Koll, A. & Przeslawska, M. Association of Diphenylguanidine and Quantum-Chemical Calculations of the Structure of Its Cyclic Dimers. Journal of Structural Chemistry 43, 412–422 (2002). https://doi.org/10.1023/A:1020328830536
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DOI: https://doi.org/10.1023/A:1020328830536