Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Design, Synthesis, and Quantum Chemical Calculations of 2,6-Diphenylspiro[cyclohexane-1,3’-pyrido[1,2-a]pyrimidine]-2’,4,4’-trione through DFT approach

Author(s): Roop Kumar, Poornima Devi, Anil K. Verma and Abha Bishnoi*

Volume 16, Issue 12, 2019

Page: [983 - 995] Pages: 13

DOI: 10.2174/1570178616666190110110123

Price: $65

Abstract

Structural elucidation of synthesized 2,6-diphenylspiro[cyclohexane-1,3’-pyrido[1,2- a]pyrimidine]-2’,4,4’-trione has been done by UV, FT-IR, 1H, 13C NMR and mass spectroscopy. The molecule was further subjected to density functional theory (DFT) studies with B3LYP function using 6-31G(d,p) basis atomic set. The title molecule was investigated on the basis of thermodynamic properties, polarizability, hyperpolarizability, intermolecular interactions, HOMO and LUMO energy values, MESP, ESP and NBO computations to correlate experimental results with in-silico studies.

Keywords: HOMO-LUMO, FT-IR, Natural Bond Orbital (NBO), MESP, ESP, Atom in Molecule (AIM).

« Previous
Graphical Abstract
[1]
Kanth, R.S.; Reddy, V.G.; Kishore, H.K.; Rao, S.P.; Narsaiah, B.; Murthy, N.S. Eur. J. Med. Chem., 2006, 41, 1011-1016.
[2]
Kurumurthy, C.; Sambasiva, R.P.; Veera, S.B.; Santhosh, K.G. Shanthan. R.P.; Narsaiah, B.; Velatooru, L.R.; Pamanji, R.; Venkateswara, R. J. Eur. J. Med. Chem., 2011, 46, 3462-3468.
[3]
Quintela, J.M.; Peinador, C.; Botana, L.; Estévez, M.; Riguera, C. Bioorg. Med. Chem., 1997, 5, 1543-1553.
[4]
El-Gazzar, B.A.; Hafez, H.N. Bioorg. Med. Chem. Lett., 2009, 19, 3392-3397.
[5]
Furuya, S.; Ohtaki, T. Chem. Abstr., 1994, 121, 205-395.
[6]
Hasan, M.F.; Madkour, A.M.; Salem, I.; Rahman, J.M.A.; Mohammed, E.A.Z. Heterocycles, 1994, 38, 57-69.
[7]
Davoll, J.; Clarke, J.; Elslager, E.F.J. Med. Chem. , 1972, 15, 837-839.
[8]
Mayer, T.U. Kapoor, T.M.; Haggarty, S.J.; King R.W.; Schreiber, T. J.; and Mitchison. Science, 1999, 286, 971-974.
[9]
Patil, A.D.; Kumar, N.V.; Kokke, W.C. J. Org. Chem., vol. 60, no. 5, pp.1182-1188
[10]
Snider, B.B.; Chen, J.; Patil, A.D.; Freyer, A.J. Tetrahedron Lett., 1996, 37, 6977-6980.
[11]
Hurst, E.W.; Hull, R. J. Med. Chem., 1961, 3, 215-229.
[12]
Ashok, M.; Holla, B.S.; Kumari, N.S. Eur. J. Med. Chem., 2007, 42, 380-385.
[13]
Bahekar, S.S.; Shinde, D.B. Bioorg. Med. Chem. Lett., 2004, 14, 1733-1736.
[14]
Broom, A.D.; Shim, J.L.; Anderson, G.L. J. Org. Chem., 1976, 41(7), 1095-1099.
[15]
Grivsk, E.M.; Lee, S.; Sigel, C.W.; Duch, D.S.; Nichol, C.A. J. Med. Chem., 1980, 23, 327-329.
[16]
Schlegel, H.B. J. Comput. Chem., 1982, 3, 214-218.
[17]
Rauhut, G.; Pulay, P. J. Phys. Chem., 1995, 99, 3093-3100.
[18]
A.P., Scott ; L., Radom J. Phys. Chem., 1996, 100, 16502-16513.
[19]
Ocola, E.J.; Brito, T.; McCann, K.; Laane, J. J. Mol. Struct., 2010, 978, 74-78.
[20]
Breda, S.; Reva, I.; Fausto, R. J. Mol. Struct., 2008, 887, 75-86.
[21]
Durig, J.R.; Ganguly, A.; El Defrawy, A.M.; Guirgis, G.A.; Gounev, T.K.; Herrebout, W.A.; Van Der Veken, B.J. J. Mol. Struct., 2009, 918, 64-76.
[22]
Durig, J.R.; Ganguly, A.; El Defrawy, A.M.; Gounev, T.K.; Guirgis, G.A. Spectrochim. Acta A, 2008, 71, 1379-1389.
[23]
Devi, P.; Fatma, S.; Bishnoi, A.; Srivastava, K.; Shukla, S.; Kumar, R. J. Mol. Struct., 2018, 1157, 551-559.
[24]
Fatma, S. Bishnoi, Abha; Verma, A.K. J. Mol. Struct., 2015, 1095, 112-124.
[25]
Shukla, S.; Bishnoi, A.; Verma, A.K.; Devi, P. ChemistrySelect, 2018, 3, 7800-7808.
[26]
Alver, Ö.; Parlak, C. J. Mol. Struct., 2010, 975, 85-92.
[27]
Alver, Ö.; Parlak, C. J. Theor. Comput. Chem., 2010, 9, 667-685.
[28]
Harayama, T.; Hori, A.; Serban, G.; Morikami, Y.; Matsumoto, T.; Abe, H.; Takeuchi, Y. Tetrahedron, 2004, 60, 10645-10649.
[29]
Druzbicki, K.; Mikuli, E.; Chrusciel, M.D.O. Vib. Spectrosc., 2010, 52, 54-62.
[30]
Güneş, E.; Parlak, C. Spectrochim. Acta A, 2011, 82, 504-512.
[31]
Liu, D. 2009. E65, 0694
[32]
Zhengyu, Z.; Aiping, F.; Dongmei, D. J. Quantum Chem, 2000, 78, 186-189.
[33]
Yoshida; H, Ehara; A, Matsuura; H. Chem. Phys. Lett., 2000, 325, 477-483.
[34]
Gupta, V.P.; Sharma, A.; Virdi, V.; Ram, V.J. Spectrochim Acta, Part A., 2006, 64, 57-67.
[35]
Glendening, E.D.; Reed, A.E.; Carpenter, J.E.; Weinhold, F. NBO Version 3.1, TCI; University of Wisconsin: Madison, 1998.
[36]
Reed, A.E.; Curtis, L.A.F. Weinhold. Chem. Rev., 1988, 88, 899-926.
[37]
Andraud, C.T.; Brotin, C.; Garcia, F.; Pelle, P.; Goldner, B. Bigot, Collet, A. J. Am. Chem. Soc., 1994, 116, 2094-2102.
[38]
Marcy, H.O.; Rosker, M.J.; Warren, L.F.; Cunningham, P.H.; Thomas, C.A.; Deloach, L.A.; Velsko, S.P.; Ebbers, C.A.; Liao, J.H.; Kanatzidis, M.G. Opt. Lett., 1995, 20, 252.
[39]
Geskin, V.M.; Lambert, C.; Bredas, J.L. J. Am. Chem. Soc., 2003, 125, 15651-15658.
[40]
Kleinman, D.A. Phys. Rev., 1962, 126, 1977-1979.
[41]
J., Bevan Ott Calculations from statistical Thermodynamics, Academic Press , 2000.
[42]
Sajan, D.; Josepha, L.; Vijayan, N.; Karabacak, M. Spectrochim. Acta, Part A, 2011, 81, 85-98.
[43]
Zhang, R.; Dub, B.; Sun, G.; Sun, Y. Spectrochim. Acta, Part A, 2010, 75, 1115-1124.
[44]
Choudhary, S.; Bee, A.; Gupta, T.P. Comput. Theor. Chem., 2013, 1016, 8-21.
[45]
Gece, G. Corros. Sci., 2008, 50, 2981-2992.
[46]
Fukui, K. Science, 1982, 218, 747-754.
[47]
Pearson, R.G. J. Org. Chem., 1989, 54, 1430-1432.
[48]
Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev., 2003, 103, 1793-1873.
[49]
Chattaraj, K.; Giri, S. J. Phys. Chem. A, 2007, 111, 11116-11121.
[50]
Rozas, I.; Alkorta, I.; Elguero, J. J. Am. Chem. Soc., 2000, 122, 11154-11161.
[51]
Matta, L.F.; Boyd, R.J. Wiley-VCH Verlag Gmbh, 2007.
[52]
Green, J.H.S.; Harrison, D.J.; Kynaston, W. Spectrochim. Acta A, 1971, 27, 2199.
[53]
Lutz, E.T.G.; Mass, J.H.V. Spectrochim. Acta A, 1986, 42, 749.
[54]
Verma, A.K.; Bishnoi, A.; Fatma, S.; Parveen, H.; Singh, V. Chemistry Select, 2017, 2, 4006-4009.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy