Isoxazole derivatives of alpha-pinene isomers: Synthesis, crystal structure, spectroscopic characterization (FT-IR/NMR/GC–MS) and DFT studies

Caramella, 1984, In 1,3-dipolar cycloaddition chemistry, vol. 1, p337 Gothelf, 1998, Chem. Rev., 98, 863, 10.1021/cr970324e Fuller, 2005, J. Am. Chem. Soc., 127, 5376, 10.1021/ja0431713 Kella-Bennani, 1995, Tetrahedron, 51, 10923, 10.1016/0040-4020(95)00668-X Tsantali, 2007, Eur. J. Org. Chem., 258, 10.1002/ejoc.200600639 Fernández-Mateos, 2005, Tetrahedron, 61, 8699, 10.1016/j.tet.2005.06.088 Kaur, 2014, Eur. J. Med. Chem., 77, 121, 10.1016/j.ejmech.2014.02.063 Banday, 2014, Steroids, 87, 93, 10.1016/j.steroids.2014.05.009 Maralinganadoddi, 2012, BMC Chem. Biol., 12, 5, 10.1186/1472-6769-12-5 Marastoni, 2014, J. Pept. Sci., 20, 258, 10.1002/psc.2612 Zhang, 2012, Carb. Res., 351, 7, 10.1016/j.carres.2011.11.025 Castellano, 2011, J. Med. Chem., 54, 7663, 10.1021/jm2010404 Jayashankara, 2008, ARKIVOC, 11, 75, 10.3998/ark.5550190.0009.b07 Gaonkar, 2007, Med. Chem. Res., 15, 407, 10.1007/s00044-006-0015-z Makriyannis, 2011, PCT Int. Appl. da Silva, 2012, Molecules, 17, 6305, 10.3390/molecules17066305 Hohenberg, 1964, Phys. Rev., 136, B864, 10.1103/PhysRev.136.B864 Kohn, 1965, Phys. Rev., 140, A1133, 10.1103/PhysRev.140.A1133 Becke, 1988, Phys. Rev. A, 38, 3098, 10.1103/PhysRevA.38.3098 Parr, 1989 Dreizler, 1990 Koch, 2001 Nowroszi, 2003, Spectrochim. Acta A, 59, 1757, 10.1016/S1386-1425(02)00410-9 Zhao, 2007, Spectrochim. Acta A, 69, 647 Benchouk, 2008, J. Mol. Struc Theochem., 852, 46, 10.1016/j.theochem.2007.12.035 İnkaya, 2013, Spectrochim. Acta A, 103, 255, 10.1016/j.saa.2012.11.039 İnkaya, 2013, Spectrochim. Acta A, 114, 92, 10.1016/j.saa.2013.05.050 Becke, 1988, J. Chem Phys., 38, 3098 Becke, 1992, J. Chem Phys., 96, 2155, 10.1063/1.462066 Becke, 1993, J. Chem Phys., 98, 5648, 10.1063/1.464913 Ditchfield, 1971, J. Chem Phys., 54, 724, 10.1063/1.1674902 Lee, 1988, Phys. Rev., 37, 785, 10.1103/PhysRevB.37.785 Sheldrick, 1997 Sheldrick, 1997 Farrugia, 1997, J. App. Cryst., 30, 565, 10.1107/S0021889897003117 Stoe & Cie, 2002 Spek, 2009, Acta Cryst. D., 65, 148, 10.1107/S090744490804362X Ditchfield, 1971, J. Chem. Phys., 54, 724, 10.1063/1.1674902 McLean, 1980, J. Chem. Phys., 72, 5639, 10.1063/1.438980 Frisch, 2009 GaussView, 2009 Hehre, 1986 Merrick, 2007, J. Phys. Chem. A, 111, 11683, 10.1021/jp073974n London, 1937, J. Phys. Radium, 8, 397, 10.1051/jphysrad:01937008010039700 McWeeny, 1962, Phys. Rev., 126, 1028, 10.1103/PhysRev.126.1028 Ditchfield, 1974, Mol. Phys., 27, 789, 10.1080/00268977400100711 Wolinski, 1990, J. Am. Chem. Soc., 112, 8251, 10.1021/ja00179a005 Cheeseman, 1996, J. Chem. Phys., 104, 5497, 10.1063/1.471789 İnkaya, 2012, J. Mol. Struc., 1027, 133, 10.1016/j.molstruc.2012.06.013 Deng, 2006, J. Org. Chem., 71, 5179, 10.1021/jo060374w Durand, 1983, Org. Magn. Reson., 21, 301, 10.1002/omr.1270210503 Gül, 2010, Can. J. Chem., 88, 323, 10.1139/V09-179 Gül, 2014, J. Het. Chem., 51, 327, 10.1002/jhet.1592 Salorinne, 2015, Acta Cryst. E, 71, 505, 10.1107/S2056989015007367 İnkaya, 2011, Acta Cryst. E, 67 Silverstein, 2005 Varsányi, 1974, 1 Raj, 2015, Spectrochim. Acta A, 147, 293, 10.1016/j.saa.2015.03.084 Furniss, 1989 Sathyanarayana, 2004 Jesson, 1958, Spectrochim. Acta A, 13, 217, 10.1016/0371-1951(58)80080-6 Mitchell, 2007 Martins, 1994, Spect. Lett. An Int. J. Rap. Comm., 27, 1227 Şen, 2015, J. Saudi Chem. Soc. Fleming, 1976 Vijayaraj, 2009, J. Chem. Theory Comput., 5, 2744, 10.1021/ct900347f Padmanabhan, 2007, J. Phys. Chem. A, 111, 9130, 10.1021/jp0718909 Zhang, 2007, J. Phys. Chem. A, 111, 1554, 10.1021/jp061633o Koopmans, 1933, Physica, 1, 104, 10.1016/S0031-8914(34)90011-2 Vektariene, 2009, 311 Mulliken, 1934, J. Chem. Phys., 2, 782, 10.1063/1.1749394 Pearson, 1963, J. Am. Chem. Soc., 85, 3533, 10.1021/ja00905a001 Pearson, 1968, J. Chem. Educ., 45, 581, 10.1021/ed045p581 Pearson, 1999, J. Chem. Educ., 2, 267, 10.1021/ed076p267 Pearson, 1986, Pro. Nat. Acad. Scie, 83, 8440, 10.1073/pnas.83.22.8440 Parr, 1983, J. Am. Chem. Soc., 105, 7512, 10.1021/ja00364a005 Parr, 1999, Am. Chem. Soc., 121, 1922, 10.1021/ja983494x Chattaraj, 2006, Chem. Rev., 106, 2065, 10.1021/cr040109f Prashanth, 2015, Opt. Photonics J., 5, 91, 10.4236/opj.2015.53008 Andraud, 1994, J. Am. Chem. Soc., 116, 2094, 10.1021/ja00084a055 Geskin, 2004, J. Am. Chem. Soc., 125, 15651, 10.1021/ja035862p Nakano, 2002, J. Am. Chem. Soc., 124, 9648, 10.1021/ja0115969 Sajan, 2006, J. Mol. Struct., 785, 43, 10.1016/j.molstruc.2005.09.041 Karakaş, 2011 Lalama, 1979, Phys. Rev. A, 20, 179, 10.1103/PhysRevA.20.1179 Sun, 2009, Antipyrine. Mol. Phys., 107, 223, 10.1080/00268970902769471 Dege, 2014, Spectrochim. Acta A, 120, 323, 10.1016/j.saa.2013.10.030 Gutowski, 1993, J. Chem. Phys., 98, 4728, 10.1063/1.465106 Prasad, 1991 Paredes, 2009, J. Mol. Struct:Theochem., 905, 76, 10.1016/j.theochem.2009.03.014 Klienman, 1962, Nonlinear dielectric polarization in optical media, Phys. Rev., 126, 1977, 10.1103/PhysRev.126.1977 Ramalingam, 2012, Spectrochim. Acta A, 96, 207, 10.1016/j.saa.2012.03.090 Suresh, 2014, Spectrochim. Acta A, 132, 130, 10.1016/j.saa.2014.04.174 Mulliken, 1955, J. Chem. Phys., 23, 1833, 10.1063/1.1740588 Pir, 2013, Spectrochim. Acta A, 112, 331, 10.1016/j.saa.2013.04.063 Sidir, 2010, J. Mol. Struct., 134, 964 Jug, 1991, 233 Fliszar, 1983 Gangadharan, 2014, Acta Phys. Pol. A, 125, 18, 10.12693/APhysPolA.125.18 Prabavathi, 2012, Spectrochim. Acta A, 99, 292, 10.1016/j.saa.2012.09.003 Li, 2011, Comput. Theor. Chem., 969, 27, 10.1016/j.comptc.2011.05.010