Home Articles List Article Information
Quarterly Journal of Iranian Chemical Communication
Journal Archive
Volume Volume 7 (2019)
Volume Volume 6 (2018)
Volume Volume 5 (2017)
Volume Volume 4 (2016)
Volume Volume 3 (2015)
Volume Volume 2 (2014)
Volume Volume 1 (2013)
Ramazani, A., Sheikhi, M., Souldozi, A., Joo, S., Yahyaei, H. (2017). Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate. Quarterly Journal of Iranian Chemical Communication, 5(Issue 4, pp. 364-493, Serial No. 17), 449-470.
Ali Ramazani; Masoome Sheikhi Sheikhi; Ali Souldozi; Sang Woo Joo; Hooriye Yahyaei. "Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate". Quarterly Journal of Iranian Chemical Communication, 5, Issue 4, pp. 364-493, Serial No. 17, 2017, 449-470.
Ramazani, A., Sheikhi, M., Souldozi, A., Joo, S., Yahyaei, H. (2017). 'Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate', Quarterly Journal of Iranian Chemical Communication, 5(Issue 4, pp. 364-493, Serial No. 17), pp. 449-470.
Ramazani, A., Sheikhi, M., Souldozi, A., Joo, S., Yahyaei, H. Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate. Quarterly Journal of Iranian Chemical Communication, 2017; 5(Issue 4, pp. 364-493, Serial No. 17): 449-470.

Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate

Article 10, Volume 5, Issue 4, pp. 364-493, Serial No. 17, Autumn 2017, Page 449-470  XML PDF (1358 K)
Document Type: Original Research Article
Authors
Ali Ramazani orcid 1; Masoome Sheikhi Sheikhi2; Ali Souldozi3; Sang Woo Joo4; Hooriye Yahyaei1
1Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan, Iran
2Young Researchers and Elite Club, Gorgan Branch, Islamic Azad University, Gorgan, Iran
3Department of Chemistry, Urmia Branch, Islamic Azad University, Urmia, Iran
4School of Mechanical Engineering, Yeungnam University, Gyeongsan 712-749, Republic of Korea
Abstract
Dimethyl (z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butenedioate has been synthesized using one-pot three component reaction between N-isocyaniminotriphenylphosphorane (Ph3PNNC), 3-methylcyclopentene-1,2-dione and dimethyl acetylenedicarboxylate. Also, optimized geometry and nuclear magnetic resonance ( NMR ) of the title compound are evaluated using HF and B3LYP methods and 6-311+G(d) basis set. Moreover, the 1H and 13C NMR chemical shift values of the molecule are calculated and compared with experimental results. Frontier molecular orbitals (FMOs), total density of states (DOS), electronic properties, natural charges, NMR parameters and NBO analysis for product were calculated by theoretical calculations. Finally, molecular electrostatic potential (MEP) surface is obtained for understanding the active regions of molecule.

Graphical Abstract

Synthesis, spectroscopic (NMR and FT-IR) and theoretical (HF and DFT) investigation of dimethyl (Z)-2-[(2-methyl-5-oxo-1-cyclopentyl)oxy]-2-butendioate
Keywords
N-Isocyaniminotriphenylphosphorane (Ph3PNNC); one-pot; DFT; NBO analysis; electronic properties
Main Subjects
Organic chemistry
References
[1] (a) Y.J Huamg, F.Y. Yang, C.J. Zhu, J. Am. Chem. Soc., 2005, 127, 16386-16387. (b) D.J. Ramn, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602-1634. (c) S. Shokrollahi, A. Ramazani, S.J. Tabatabaei Rezaei, A. Mashhadi Malekzadeh, P. Azimzadeh Asiabi, S. W. Joo, Iran. J. Cat., 2016, 6, 65-68. (d) O.P. Priest, M. Serafin, J. Chem. Educ., 2015, 92, 595-597. (e) N. Elder, D.V.D. Born, L.J.D. Hendrickx, B.J.J. Timmer, A. Krause, E. Janssen, F.J.J. D. Kanter E. Ruijter, R.V.A. Orru, Angew. Chem. Int. Ed., 2009, 48, 5856-5859. (f) M. Rouhani, A. Ramazani, S. W. Joo, Ultrason. Sonochem., 2016, 28, 393-399. (g) A. Ramazani, A. Rezaei, A. Tofangchi Mahyari, M Rouhani, M. Khoobi, Helv. Chim. Acta, 2010, 93, 2033-2036. (h) A. Ramazani, Y. Ahmadi, F. Zeinali Nasrabadi, Z. Naturforsch., 2011, (66b), 184-190. (i) A. Ramazani, F. Zeinali Nasrabadi, A. Mashhadi Malekzadeh, Y. Ahmadi, Monatsh Chem., 2011, 142, 625-630. (j) A. Souldozi, K. Ślepokura, T. Lis, A. Ramazani, Z. Naturforsch., 2007, 62b, 835-840. (k) A. Ramazani, A. R. Kazemizadeh, Curr. Org. Chem., 2011, 15, 3986-4020. (l) A. Ramazani, A. Rouhani, E. Mirhadi, M. Sheikhi, K. Ślepokura, T. Lis, Nano. Chem. Res., 2016, 1, 87-107. (m) A. Ramazani, A. Bodaghi, A. Phosphorus Sulfur Silicon Relat. Elem., 2004, 179, 1615-1620. (n) A. Ramazani, M. Rahimifard, Phosphorus Sulfur Silicon Relat. Elem., 2006, 181, 2675-2678. (o) A. Ramazani, A. Souldozi, Phosphorus Sulfur Silicon Relat. Elem., 2005, 180, 2801-2804. (p) A. Ramazani, A. Souldozi, Phosphorus Sulfur Silicon Relat. Elem., 2003, 178, 1325-1328. (q) A. Ramazani, H. Ahankar, Phosphorus, Sulfur, Silicon Relat. Elem., 2001, 170, 181-185. (r) I. Yavari, A. Ramazani, Synth. Commun., 1997, 27, 1385-1390. (s) F.Z. Nasrabadi, A. Ramazani, Y. Ahmadi, Mol. Divers., 2011, 15, 791-798. (t) A. Ramazani, A. Souldozi, Phosphorus Sulfur Silicon Relat. Elem., 2004, 179, 529-533. (u) A. Ramazani, A. Souldozi, Phosphorus Sulfur Silicon Relat. Elem., 2003, 178, 1329-1332. (v) M. Khoobi, S. Emami, G. Dehghan, A. Foroumadi, A. Ramazani, A. Shafiee, Arch. Pharm., 2011, 344, 588-594.(w) M. Khoobi, A. Foroumadi, S. Emami, M. Safavi, G. Dehghan, B. Heidary Alizadeh, A. Ramazani, S.K. Ardestani, A. Shafiee, Chem. Biol. Drug. Des., 2011, 78, 580-586. (x) A. Ramazani, A. Souldozi, A. Phosphorus Sulfur Silicon Relat. Elem., 2003, 178, 2663-2666. (y) M.H. Gonbari, A. Ramazani, A. Souldozi, Phosphorus Sulfur Silicon Relat. Elem., 2009, 184, 309-314. (z) R. Arabian, A. Ramazani, B. Mohtat, A. Azizkhani, S. W. Joo, M. Rouhani, J. Energ. Mater., 2014, 32, 300-305.

[2] (a) V.P. Boyarskiy, N.A. Bokach, K. V. Luzyanin, V.Y. Kukushkin, Chem. Rev., 2015, 115, 2698-2779. (b) Y. Xu, X. Hu, J. Shao, G. Yang, Y. Wu, Z. Zhang, Green Chem., 2015, 17, 532-537. (c) E. Gonzalez-Fernandez, J. Rust, M. Alcarazo, Angew., Chem. Int. Ed., 2013, 52, 11392-11395. (d) J. Taran, A. Ramazani, S.W. Joo, K. Ślepokura, T. Lis, Helv. Chim. Acta, 2014, 97, 1088-1096. (e) E. Vessally, A. Ramazani, E. Yaaghubi, Monatsh Chem., 2011, 142, 1143-1147. (f) N. Shajari, A. Ramazani, Phosphorus, Sulfur Silicon Relat. Elem., 2010, 185, 1850-1857. (g) A. Ramazani, A. Souldozi, R. Ghadimi, Y. Ahmadi, V. Azizkhani, P. Azimzadeh Asiabi, Org Chem: An Indian Journal, 2015, 11, 229-233. (h) A. Ramazani, F. Zeinali Nasrabadi, Z. Karimi, M. Rouhani, Bull. Korean Chem. Soc., 2011, 32, 2700-2704. (i) A. Ramazani, A. Souldozi, Arkivoc, 2008, (xvi), 235-242. (j) H. Javanbani, A. Ramazani, S. W. Joo, Y. Ahmadi, V. Azizkhani, P. Azimzadeh Asiabi, Iran. Chem. Commun., 2015, 3, 310-322. (k) A.R. Kazemizadeh, A. Ramazani, Arkivoc, 2008, xv, 159-165. (l) A.R. Kazemizadeh, A. Ramazani, J. Braz. Chem. Soc., 2009, 20, 309-312. (m) A. R. Kazemizadeh, A. Ramazani, Curr. Org. Chem., 2012, 15, 418-450.

[3] W. Lieke, Justus Liebigs Ann. Chem., 1859, 112, 316-321.

[4] (a) M. Passerini and L. Simone, Gazz. Chim. Ital., 1921, 51, 126-129. (b) M. Passerini, Gazz. Chim. Ital., 1921, 51, 181-188.

[5] (a) A. Dömling, Chem. Rev., 2006, 106, 17-89. (b) P. Molina, M.J. Vilaplana, Synthesis, 1994, 12, 1197-1218. (c) S. Ayesa, B. Samuelsson, B. Classon, B. Synlett, 2008, 1, 97-99.

[6] (a) H. Stolzenberg, B. Weinberger, W.P. Fehlhammer, F.G. Pühlhofer, R. Weiss, Eur. J. Inorg. Chem., 2005, 21, 4263-4271. (b) T.W. Chiu, Y.H. Liu, K. M. Chi, Y.S. Wen, K.L. Lu, Inorg. Chem., 2005, 44, 6425-6430.

[7] (a) A. Souldozi, A. Ramazani, Tetrahedron Lett., 2007, 48, 1549-1551. (b) A. Ramazani, M. Rouhani, A. Rezaei, N. Shajari, A. Souldozi, Helv. Chim. Acta, 2011, 94, 282-288. (c) A. Ramazani, Y. Ahmadi, R. Tarasi, Heteroat. Chem., 2011, 22, 79-84. (d) A. Ramazani, F. Zeinali Nasrabadi, Y. Ahmadi, Helv. Chim. Acta, 2011, 94, 1024-1029. (e) A. Ramazani, S. Salmanpour, A. Souldozi, Phosphorus, Sulfur, Silicon Relat. Elem., 2010, 185, 97-102. (f) A. Ramazani, N. Shajari, A. Tofangchi Mahyari, M. Khoobi, Y. Ahmadi, A. Souldozi, Phosphorus, Sulfur, Silicon Relat. Elem., 2010, 185, 2496-2502. (g) A. Ramazani, M. Rouhani, F. Zeinali Nasrabadi, F. Gouranlou, Phosphorus, Sulfur, Silicon Relat. Elem., 2015, 190, 20-28. (h) M. Rouhani, A. Ramazani, S.W. Joo, Ultrason. Sonochem. 2015, 22, 391-396. (i) M. Rouhani, A. Ramazani, S. W. Joo, Ultrason. Sonochem, 2014, 21, 262-267. (j) A. Ramazani, Y. Ahmadi, Z.  Karimi, A. Rezaei, J. Heterocyclic Chem., 2012, 49, 1447-1451. (k) A. Ramazani, F. Zeinali Nasrabadi, B. Abdian, M. Rouhani, Bull. Korean Chem. Soc., 2012, 33, 453-458. (l) M. Valizadeh Holagh, A.M. Maharramov, M.A. Allahverdiyev, A. Ramazani, Y. Ahmadi, A. Souldozi, Turk. J. Chem., 2012, 36, 179-188. (m) A. Ramazani, Z. Karimi, A. Souldozi, Y. Ahmadi, Turk. J. Chem., 2012, 36, 81-91. (n) A. Ramazani, A. Rezaei, Org. Lett., 2010, 12, 2852-2855. (o) A. Ramazani, N. Fattahi, A. Rezaei, F. Zeinali Nasrabadi, Chemija, 2012, 23, 255-261. (p) A. Ramazani, A. Rezaei, Y. Ahmadi, Phosphorus, Sulfur Silicon Relat. Elem., 2012, 187, 22-31. (q) A. Ramazani, F. Zeinali Nasrabadi, Z. Karimi, M. Rouhani, Synth. Commun., 2013, 43, 1818-1830. (r) A. Ramazani, M. Ashtari, A. Souldozi, Y. Ahmadi, Phosphorus, Sulfur Silicon Relat. Elem., 2012, 187, 1064-1073. (s) A. Ramazani, Y. Ahmadi, A.M. Malekzadeh, A. Rezaei, Heteroatom Chem., 2011, 22, 692-698. (t) A. Ramazani, M. Khoobi, A. Torkaman, F. Zeinali Nasrabadi, H. Forootanfar, M. Shakibaie, M. Jafari, A. Ameri, S. Emami, M.A. Faramarzi, A. Foroumadi, A. Shafiee, Eur. J. Med. Chem., 2014, 78, 151-156. (u) H. Ahankar, A. Ramazani, Y. Ahmadi, Phosphorus, Sulfur, Silicon Relat. Elem., 2014, 189, 914-923. (v) H. Ahankar, A. Ramazani, I. Amini, Y. Ahmadi, A. Souldozi, Heteroat. Chem., 2011, 22, 612-616. (w) N. Shajari, A. R. Kazemizadeh, A. Ramazani, J. Serb. Chem. Soc., 2012, 77, 1175-1180. (x) A. Ramazani, B. Abdian, F.Z. Nasrabadi, N. Shajari, Z. Ranjdoost, Bull. Korean Chem. Soc., 2012, 33, 3701-3705. (y) N. Shajari, A. R. Kazemizadeh, A. Ramazani, Turk. J. Chem., 2015, 39, 874-879. (z) A. Ramazani, R. Kalhor, A. Rezaei, Z. Karimi, Heteroat. Chem., 2012, 23, 315-321.

[8] A. Ramazani, S. Salmanpour, A. Souldozi, Phosphorus, Sulfur, and Silicon Relat. Elem., 2010, 185, 97-102.

[9] I. Yavari, A. Ramazani, Synth. Commun., 1996, 26, 4495-4499.

[10] I. Yavari, A. Ramazani, Phosphorus Sulfur and Silicon, 1997, 130, 73-77.

[11] A. Ramazani, A. Bodaghi, Tetrahedron Lett., 2000, 41, 567-568.

[12] P. Pakravan, A. Ramazani, N. Noshiranzadeh, A. Sedrpoushan, Phosphorus, Sulfur, and Silicon, 2007, 182, 545-549.

[13] A. Ramazani, M. Rahimifard, A. Souldozi, Phosphorus, Sulfur, and Silicon, 2007, 182, 1-5.

[14] A. Ramazani, M. Rahimifard, N. Noshiranzadeh, A. Souldozi, Phosphorus, Sulfur, and Silicon, 2007, 182, 413-417.

[15] I. Yavari, A. Ramazani, A. Yahya-Zadeh, Synth. Commun., 1996, 26, 4495-4499.

[16] A. Ramazani, E. Ahmadi, A.R. Kazemizadeh, L. Dolatyari, N. Noshiranzadeh, I. Eskandari, A. Souldozi, Phosphorus, Sulfur, and Silicon, 2005, 180, 2419-2422.

[17] A. Ramazani, M. Mohammadi-Vala, Phosphorus Sulfur and Silicon, 2001, 176, 223-229.

[18] A. Ramazani, I. Amini, A. Massoudi, Phosphorus Sulfur and Silicon, 2006, 181, 2225-2229.

[19] A. Souldozi, A. Ramazani, N. Bouslimani, R. Welter, Tetrahedron Lett., 2007, 48, 2617-2620.

[20] Souldozi, A. Ramazani, Tetrahedron Lett., 2007, 48, 1549-1551.

[21] A. Ramazani, A. Morsali, B. Ganjeie, A.R. Kazemizadeh, E. Ahmadi, R. Kempe, I. Hertle, Z. Naturforsch., 2005, 60b, 569-571.

[22] A. Ramazani, S.A. Hossaini-Alemi, Phosphorus Sulfur and Silicon, 2001, 176, 237-266.

[23] A. Ramazani, A. Souldozi, Phosphorus Sulfur and Silicon, 2003, 178, 1325-1328.

[24] A. Ramazani, A. Souldozi, Phosphorus Sulfur and Silicon, 2003, 178, 1329-1332.

[25] A. Ramazani, A. Souldozi, Phosphorus Sulfur and Silicon, 2003, 178, 2663-2666.

[26] A. Ramazani, E. Ahmadi, Phosphorus Sulfur and Silicon, 2003, 178, 2659-2661.

[27] A. Ramazani, A. Souldozi, Phosphorus Sulfur and Silicon, 2004, 179, 529-533.

[28] A. Ramazani, A. Bodaghi, Phosphorus Sulfur and Silicon, 2004, 179, 1615-1620.

[29] A. Ramazani, A.R. Kazemizadeh, E. Ahmadi, Phosphorus Sulfur and Silicon, 2005, 180, 1781-1784.

[30] A. Ramazani, A. Azizian, M. Bandpey, N. Noshiranzadeh, Phosphorus Sulfur and Silicon, 2006, 181, 2731-2734.

[31] A. Ramazani, E. Ahmadi, Phosphorus Sulfur and Silicon, 2006, 181, 2725-2729.

[32] M. Mozaffarieh, M. C. Grieshaber, S. Orgül, J. Flammer, Surv Ophthalmol., 2008, 53, 479-505.

[33] J.H. Chung, S.Y. Choi,  J.Y. Kim, D.H. Kim, J.W.  Lee,  J.S. Choi, H.Y. Chung, J. Agric. Food Chem., 2007, 55, 6787-6792.

[34] D. Avci, Y. Atalay, Struct. Chem., 2009, 20, 185-201. b) R. B.Nazarski, J. Phys. Org. Chem., 2009, 22, 834-844.

[35] S.M. Shoaei, A.R. Kazemizadeh, A. Ramazani, Chin. J. Struct. Chem., 2011, 30, 568-574.

[36] H. Hopfl, B. Gomez, R. Martinez-Palou, J. Mex. Chem. Soc., 2005, 49, 307-311.

[37] P.C. Hariharan, J.A. Pople, Theor. Chim. Acta, 1973, 28, 213-322.

[38] P.C. Hariharan, J.A. Pople, Mol. Phys., 1974, 27, 209-214.

[39] W. Kohn, A.D. Becke, R.G. Parr, J. Phys. Chem., 1996, 100, 12974-12980.

[40] M.J. Frisch et al., Gaussian 09, Revision A.1, Gaussian Inc., Wallingford, CT, 2009.

[41] A. Soltani, F. Ghari, A. Dehno Khalaji, E. Tazikeh Lemeski, K. Fejfarova, M. Dusek, M. Shikhi, Mol. Biomol. Spectro., 2015, 139, 271-277.

[42] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian, Inc., Wallingford CT, 2009.

[43] A. Suvitha, S. Periandy, M. Govindarajan, P. Gayathri, Mol. Biomol. Spectrosc., 2015, 138, 900-912.

[44] M. Sheikhi, D. Sheikh, A. Ramazani, S. Afr. J. Chem., 2014, 67, 151-159.

[45] B.D. Joshi, P. Tandon, S. Jain, The Himalayan Physics., 2012, 3, 44-49.

[46] D. Habibi, A.R. Faraji, D. Sheikh, M. Sheikhi, S. Abedi, RSC Adv., 2014, 4, 47625-47636.

[47] K.G. Vipin Das, C. Yohannan Panicker, B. Narayana, P.S. Nayak, B. K. Sarojini, A.A. Al-Saadi, Mol. Biomol. Spectrosc., 2015, 135, 162-171.

[48] L. Shiri, D. Sheikh, M. Sheikhi, Rev. Roum. Chim., 2014, 59, 825-834.

[49] A.R. Soltani, M.T. Baei, M. Mirarab, M. Sheikhi, E. Tazikeh Lemeski, J. Phys. Chem. Solids, 2014, 75, 1099-1105.

[50] K. Chandrasekaran, R. Thilak Kumar, Mol. Biomol. Spectrosc., 2015, 150, 974-991.

[51] K. Fukui, Science, 1982, 218, 747-754.

[52] S. Gunasekaran, R.A. Balaji, S. Kumeresan, G. Anand, S. Srinivasan, Can. J. Anal. Sci. Spectro., 2008, 53, 149-162.

[53] R.G. Parr, R.A. Donnelly, M. Levy, W.E. Palke, J. Chem. Phys., 1978, 68, 3801-3807.

[54] R.G. Parr, W. Yang, J. Am. Chem. Soc., 1984, 106, 4049-4050.

[55] M. Sheikhi, D. Sheikh, Rev. Roum. Chim., 2014, 59, 761-767.

[56] F. Weinhold, C.R. Landis, Natural Bond Orbitals and Extensions of Localized, 2001.

[57] S. Guidara, A.B. Ahmed, Y. Abid, H. Feki, Mol. Biomol. Spectrosc., 2014, 127, 275-285.

 

Statistics
Article View: 1,087
PDF Download: 691