The Bonds Analysis of Hexamethylenetetramine

• Autorzy: Trzęsowska A. , Kruszyński R.
• Języki publikacji: EN

Abstrakty

EN

Natural Bond Orbital (NBO) method was used for the investigation of the hexamethylenetetramine (hmt). The nature of bonds and electronic properties of the titled compound were analysed by means of quantum mechanical calculations on the structural molecular geometries from neutron diffraction measurements carried out in seven, different temperatures. Calculations were performed using density functional theory method (B3LYP) with 6-31++G(d,p) basis set. The values of total and stabilization energy, orbital populations, vibrational frequencies, dipole moments are discussed. As expected, the total hmt energy value decreases as the temperature decreases. The most profitable energy value was obtained for the lowest hmt measurement temperature, which implies that the significant and favourable reduction of thermal motion took place. The geometric parameters of hmt molecule are similar in all structures, the only normality is the shortening and hence enhancing of C-N bond with the temperature increasing. The NBO analysis of donor-acceptor interactions resulted in decreasing of localized nN, sigma CH orbital occupancy, increasing of CN * occupancy and stabilization energy associated with following delocalizations: nN sigma CN * and sigma CH sigma CN * . The results indicated that there exist very slight interactions between this nitrogen pair and the C-H antibonding orbitals of nearest neighbouring hmt molecule when the sets of hmt molecules are considered.

Słowa kluczowe

EN

hexamethylenetetramine (HTM); natural bond orbital analysis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 7
• Strony: 1155--1168
• Opis fizyczny: Bibliogr. 28 poz., rys.

Twórcy

autor

Trzęsowska A.

• Department of X-Ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Technical University of Lodz, Zeromskiego 116, 90-924 Lodz, Poland

autor

Kruszyński R.

• Department of X-Ray Crystallography and Crystal Chemistry, Institute of General and Ecological Chemistry, Technical University of Lodz, Zeromskiego 116, 90-924 Lodz, Poland

Bibliografia

• 1.Butlerow A., Ann., 111, 250 (1859).
• 2.Svensson P.H., Bengtsson-Kloo L.A. and Stegemann H., Acta Cryst., C51, 2289 (1995).
• 3.Kampermann S.P., Ruble J.R. and Craven B.M., Ada Cryst., B50, 737 (1994).
• 4.International Tables for Crystallography Vol. A, Ed. T. Hahn, Dordrecht, Holland 1983, pp. 652-653:
• 5.Wu S., Lantai Gongye, 20(11), 665 (2000); Ismail H., RosnahN. and Rozman H.D., European Polymer Journal, 33, 1231 (1997); Wenjie C., Jian W. and Ming J., Polymer, 39, 2867 (1998); Suhara F., Kutty S.K.N. and Nando G.B., Plastics, Rubber & Composites Processing and Appl, 24, 37 (1995).
• 6.Wang W„ Faming Zhuanli Shenqing Gonghai Shuomingshu, CN 1,231,347 (Cl. C23F11 /167) (1999)Choi Y.-S., Chung M.-K. and Kim J.-G., Materials Science and Engineering: A, 384, 47 (2004); Singh D.D.N., Singh T.B. and GaurB., Corrosion Science, 37, 1005 (1995); Gao Y.-M., MaX.-J., Fang L., Zhang X.-F. and Su J.-Y., Wear. 248,1 (2001); Hosseini M., Mertens S.F.L. and Arshadi M.R Corrosion Science, 45, 1473 (2003).
• 7.Peter-Hoblyn J.D., PCTInt. Appl., WO 95 02,655 (Cl. C10L1/30) (1995).
• 8.Jacobs W.A. and Heidelberger M., J. Biol. Chem., 20, 659(1915); Jacobs W.A., J. Exp. Med., 23, 5 (1916); Massi L., Guittard F., Geribaldi S., Levy R. and Duccini Y., Int. J. Antimicrobial Agents, 21, (2003).
• 9.Bernstein M.P., Sandford S.A., Allamandola L.J. and Chang S., J. Phys. Chem., 98, 12206 (1994)
• Bemstein M.P., Allamandola L.J. and Sandford S.A., Advances in Space Research, 19, 991 (1997)'
• Chamley S.B., Rodgers S.D., Kuan Y.-J. and Huang H.-C., Advances in Space Research, 30, 14 (2002); Cottin H., Bachir S., Raulin F. and Gazeau M.-C., Advances in Space Research, 30,1481 (200; Cottin H., Gazeau M.C. and Raulin F., Planetary and Space Science, 47, 1141 (1999).
• 10.Galasso V., Chem. Phys., 270, 79 (2001).
• 11.Galasso V., J. Mol Struct. (Theochem), 336, 47 (1995).
• 12.Litvinyuk I.V., Young J.B., Zheng Y., Cooper G. and Brion C.E., Chem. Phys., 263, 195 (2001).
• 13.Reed A.E., Curtis L.A. and Weinhold F.A., Chem. Rev., 88, 899 (1988).
• 14.Foster J.P. and Weinhold F.A., J. Am. Chem. Soc., 102, 7211 (1980).
• 15.Reed A.E. and Weinhold F.A., J. Chem. Phys., 83, 1736 (1985).
• 16.Ebrahimi A., Deyhimi F. and Roohi H., J. Mol. Struct. (Theochem), 626, 223 (2003).
• 17.Kampermann S.P., Sabine T.M., Craven B.M. and McMullan R.K., Acta Cryst., AS1, 489 (1995).
• 18.Terpstra M., Craven M. and Stewart R.F., Acta Cryst., A49, 685 (1993).
• 19.Frisch M.J., Trucks G.W., Schlegel H.B., ScuseriaG.E., Robb M.A., Cheeseman J.R., Montgomery J./ Vreven Jr., T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci E Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukui R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.I Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador i Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K, Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M. W., Johnson B., Chen V Wong M. W., Gonzalez C., Pople J.A., Gaussian 03, Revision A. 1, Gaussian, Inc., Pittsburgh PA. 2003.
• 20.Cramer C.J., Essential of Computational Chemistry. Theories and Models, John Wiley & Sons LTI West Sussex 2002.
• 21.Bader R.F.W., Atoms in Molecules. A Quantum Theory, Oxford University Press, Oxford 1990.
• 22.Reed A.E. and Schleyer P.R., Inorg. Chem., 27, 3969 (1988).
• 23.Bertie J.E. and Solinas M., J. Chem. Phys., 61, 1666 (1974).
• 24.Bernstein M.P., Sandford S.A., Allamandola L.J. and Chang S., J. Phys. Chem., 98, 12206 (1994).
• 25.Jensen J.O., Spectrochim. Acta, A58, 1374 (2002).
• 26.Williams R.V., Gadgil V.R., Luger P., Koritsanszky T. and Weber M„ J. Org. Chem., 64, 1180 (1995
• 27.Zobel D., Luger P., Dreissig W. and Koritsanszky T., Acta Cryst., B48, 837 (1992).
• 28.Koritsanszky T., Zobel D. and Luger P., J. Phys. Chem., A104, 1549 (2000).