Ultrasonic and Spectral Studies on Hydrogen Bonded Complexes of Aromatic Aldehydes and N-Methylaniline in n-Hexane

R. Kumar; B.S. Santhi; Vijayakanth Mr.; V. Kannappan

doi:10.6000/1929-5030.2013.02.03.5

Authors

R. Kumar New College, Chennai 600014
B.S. Santhi Presidency College, Chennai 600005
Vijayakanth Mr. DG Vaishnav College, Chennai 600106
V. Kannappan Presidency College, Chennai600005, India

DOI:

https://doi.org/10.6000/1929-5030.2013.02.03.5

Keywords:

Aldehyde-amine H-bonded complex, stability constants, structural effect

Abstract

Ultrasonic and UV-spectral studies have been carried out for three ternary systems containing N-methylaniline (NMANI) and three structurally different aromatic aldehydes, benzaldehyde (BA), cinnamaldehyde (CA) and salicylaldehyde(SA) in n-hexane medium at 303.15 K and at atmospheric pressure. Acoustical parameters are computed from the measured values of ultrasonic velocity, density and dynamic viscosity. The variation of acoustical parameters in the concentration range investigated establishes complex formation through intermolecular hydrogen bonding between aldehyde and N-methylaniline. The existence of strong aldehyde-amine interaction is also confirmed through the recorded UV-Visible absorption spectra with Benesi-Hildebrand theory at 303.15 K. The formation constants of the hydrogen bonded complexes are determined by spectroscopic and ultrasonic methods and compared. These values computed by two different methods are comparable and follow similar trend. The trend in the formation constants is discussed based on structures of the component molecules and correlate with computed molecular properties

Author Biographies

R. Kumar, New College, Chennai 600014

Department of Physics

B.S. Santhi, Presidency College, Chennai 600005

Department of Chemistry

Vijayakanth Mr., DG Vaishnav College, Chennai 600106

Department of Physics

V. Kannappan, Presidency College, Chennai600005, India

Department of Chemistry

References

[1] Oswal SL, Gardas RL, Phalak RP. Densities, speeds of sound, isentropic compressibilities, refractive indices and viscosities of binary mixtures of tetrahydrofuran with hydrocarbons at 303.15 K. J Mol Liq 2005; 116: 109-18. http://dx.doi.org/10.1016/j.molliq.2004.07.081
[2] Ali A, Nain AK, Sharma VK, Ahmad S. Study of molecular interaction in ternary mixtures through ultrasonic speed measurements. Phys Chem Liq 2004; 42: 375-83. http://dx.doi.org/10.1080/00319100410001679882
[3] Kumar R, Swarnalathan S, Mahesh R, Shanmugapriyan B, Kannappan V. Ultrasonic and spectroscopic studies on hydrogen bonded complexes of aromatic amine and aryl ketones inn-hexane at 303.15 K. J Mol Liq 2011; 163: 57-63. http://dx.doi.org/10.1016/j.molliq.2011.07.010
[4] Kumar R, Ulagendran V, Kannappan V, Jayakumar S. Thermo acoustic and spectral investigations of charge transfer interaction between aromatic amine and ketones. Fluid Phase Equlibria 2011; 307: 113-25. http://dx.doi.org/10.1016/j.fluid.2011.04.019
[5] Kumar R, Jayakumar S, Kannappan V. Thermodynamic properties of donor–acceptor complexes of tertiary amine with aryl ketones in hexane medium. Thermochimica Acta 2012; 536: 15-23. http://dx.doi.org/10.1016/j.tca.2012.02.018
[6] Parsons Andrew F. Keynotes in organic chemistry, Blackwell Science Limited, London, Oxford 2003; p. 2.
[7] Cai J, Wang RE, Eds. Protein Interactions, Published by InTech, Janeza Trdine Rijeka, Croatia 2012; p. 9.
[8] Higuchi T, Lachman L. Inhibition of hydrolysis of esters in solution by formation of complexes III. Stabilization of tetracaine with caffeine. J Am Pharm Associ 1957; 46: 32-36.
[9] Andrews JL, Keefer RM. Molecular complexes in Organic Chemistry, London, Holden- Day, Inc 1964; p. 7.
[10] Vogel AI. A Textbook of Practical Organic Chemistry, 5th ed. New York, John Wiley 1989.
[11] Weissberger A, Prokaher FS, Reddick JA, Toops EE. Techniques of Organic Chemistry, vol VII, Organic Solvents, New York, Interscience 1955.
[12] Baldevraj, Rajendran V, Palanichamy. Science and Technology of Ultrasonics, New Delhi, Narosa Publications 2004.
[13] Kannappan V, Jaya Santhi R. Ultrasonic investigation of induced dipole-induced dipole interactions in binary liquid mixtures at 298K. Ind J Pure Appl Phys 2006; 44: 815-19.
[14] Ishwara Bhat J, Manjunatha MN, Shree Varaprasad NS. Acoustic behaviour of citric acid in aqueous and partial aqueous media. Ind J Pure Appl Phys 2010; 48: 875-80.
[15] Ulagendran V, Kumar R, Jayakumar S, Kannappan V. Ultrasonic and spectroscopic investigations of charge transfer complexes in ternary liquid mixtures. J Mol Liq 2009; 148: 67-72. http://dx.doi.org/10.1016/j.molliq.2009.06.012
[16] Vibhu I, Singh AK, Gupta M, Shukla JP. Ultrasonic and IR investigation of N-H ----- N complexes in ternary mixtures. J Mol Liq 2004; 115: 1-3. http://dx.doi.org/10.1016/j.molliq.2003.08.024
[17] Awasthi A, Rastogi M, Gupta M, Shukla JP. Ultrasonic investigation of molecular association in ternary mixtures. J Mol Liq 1999; 80: 77-84. http://dx.doi.org/10.1016/S0167-7322(99)00016-1
[18] Palaniappan L. Ultrasonic analysis in the ternary system of pyridine + benzene + 2-butanol. Physica 2008; B403: 3887- 91.
[19] Kannapan AN, Kesavasamy R, Ponnuswamy V. Molecular interaction studies in the ternary liquid mixture of pyridine + benzene + N, N-dimethylformamide by ultrasonic velocity measurements. ARPN J Eng Appl Sci 2008; 3: 41-45.
[20] Mulliken RS, Pearson WB. Molecular Complexes - A lecture and Report volume, New York, Wiley Publishers 1969.
[21] Foster R. Organic Charge-transfer Complexes, London, Academic Press 1969; p. 387.
[22] Benesi HA, Hildebrand JH. A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. J Am Chem Soc 1949; 71: 2703-2007. http://dx.doi.org/10.1021/ja01176a030
[23] Foster R, Ed. Molecular Complexes, London, Elek Science 1973; Vol. 1.