Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety
Yıl: 2019 Cilt: 6 Sayı: 3 Sayfa Aralığı: 223 - 228 Metin Dili: İngilizce DOI: 10.17350/HJSE19030000151 İndeks Tarihi: 11-06-2020
Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety
Öz: The conformational analyses of Calix[4]arenes reveals four different stable structures(conformations); Cone, Partial Cone, 1,2-Alternate and 1,3-Alternate after employinga density functional theory (DFT) computational analysis. Intramolecular HydrogenBonds (IHBs) existing Calixarene core cause Cone conformation, supporting to be the beststable state in 1, 2 and 3 compounds. In addition, one needs Natural Bond Orbital (NBO)analyses of current compounds in order to understand nature of these IHBs. Specifically,it has been shown using NBO that the LP *→σ interactions for O˙˙˙O¯H IHBs and thedelocalization LP → π* for O¯C=O are the major contributions to energy stabilization. Ofall conformers of compound 4, Partial Cone has the lowest energy, which can be attributedto devoid of intramolecular hydrogen bond due to the absence of free phenolic groups.
Anahtar Kelime: Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
- 1. Gutsche CD. Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, UK, 1998.
- 2. Furer VL, Potapova LI, Vatsouro IM, Kovalev VV, Shokova EA, Kovalenko VI. Investigation of the conformation and hydrogen bonds in adamantylthiacalix[4]arene by IR spectroscopy and DFT. Journal of Molecular Structure 1171 (2018) 207-213.
- 3. Şener İ, Şener N, Erişkin S. Synthesis and absorption spectra of some novel hetaryltetrakisazocalix[4]arene derivatives. Dyes and Pigments 96(1) (2013) 256-263
- 4. Galindo-Murillo R, Olmedo-Romero A, Cruz-Flores E, Petrar PM, Kunsagi-Mate S, Barroso-Flores J. Calix[n]arene-based drug carriers: A DFT study of their electronic interactions with a chemotherapeutic agent used against leukemia. Computational and Theoretical Chemistry 1035 (2014) 84-91.
- 5. Shamova LI, Shamov GA, Antipin IS, Konovalov AI. Modeling K + and Ag + Complexation by Thiacalix[4]arene Amides Using DFT: The Role of Intramolecular Hydrogen Bonding. The Journal of Physical Chemistry A 113 (19) (2009) 5691-5699.
- 6. Bifulco G, Gomez-Paloma L, Riccio R, Gaeta C, Troisi F, Neri P. Quantum Mechanical Calculations of Conformationally Relevant 1 H and 13 C NMR Chemical Shifts of Calixarene Systems. Organic Letters 7(26) (2005) 5757-5760.
- 7. Guzzo RN, Rezende MJC, Kartnaller V, Carneiro JW de M, Stoyanov SR, Costa da LM. Experimental and DFT evaluation of the 1H and 13C NMR chemical shifts for calix[4]arenes. Journal of Molecular Structure 1157 (2018) 97-105.
- 8. Kostyukevych KV, Khristosenko RV, Pavluchenko AS, Vakhula AA, Kazantseva ZI, Koshets IA, Shirshov YM. A nanostructural model of ethanol adsorption in thin calixarene films. Sensors and Actuators B: Chemical 223 (2016) 470-480.
- 9. Özkınalı S, Kocaokutgen H. Synthesis, spectral characterisation and thermal behaviours of some new p-tert-butylcalix[4]arene and calix[4]arene-esters containing acryloyl groups. Journal of Molecular Structure 1031 (2013)70-78.
- 10. Özkinali S, Uçar I, Kocaokutgen H, Bulut A. 25,27-Bis(acryloyloxy)- 26,28-dihydroxycalix[4]arene toluene hemisolvate. Acta Crystallographica Section E Structure Reports Online 63(8) (2007) o3378-o3378.
- 11. Roy D, Todd K, John M. GaussView, Version 5, Semichem Inc., Shawnee Mission, KS, 2009.
- 12. Walters P, Stahl M. Babel, Version 1.1, Department of Chemistry, University of Arizona, Tucson, AZ 85721.
- 13. Frisch MJ, Trucks WG, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, and Fox DJ. Gaussian 09, Revision C.01, Gaussian, Inc., Wallingford CT, 2010.
- 14. Glendening ED, Reed AE, Carpenter JE, Weinhold F. NBO Version 3.1, TCI, University of Wisconsin, Madison, 1998.
- 15. Özkınalı S, Karayel A. Synthesis, characterization, conformational equilibrium and intramolecular hydrogen bond analysis of Novel Azocalix[4]arenes including acryloyl moiety using DFT studies. Journal of Molecular Structure 1176 (2019) 303-313.
- 16. Chawla HM, Singh SP, Sahu SN, Upreti S. Shaping the cavity of calixarene architecture for molecular recognition: synthesis and conformational properties of new azocalix[4]arenes. Tetrahedron 62(33) (2006) 7854-7865.
| APA | KARAYEL A (2019). Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. , 223 - 228. 10.17350/HJSE19030000151 |
| Chicago | KARAYEL ARZU Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. (2019): 223 - 228. 10.17350/HJSE19030000151 |
| MLA | KARAYEL ARZU Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. , 2019, ss.223 - 228. 10.17350/HJSE19030000151 |
| AMA | KARAYEL A Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. . 2019; 223 - 228. 10.17350/HJSE19030000151 |
| Vancouver | KARAYEL A Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. . 2019; 223 - 228. 10.17350/HJSE19030000151 |
| IEEE | KARAYEL A "Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety." , ss.223 - 228, 2019. 10.17350/HJSE19030000151 |
| ISNAD | KARAYEL, ARZU. "Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety". (2019), 223-228. https://doi.org/10.17350/HJSE19030000151 |
| APA | KARAYEL A (2019). Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. Hittite Journal of Science and Engineering, 6(3), 223 - 228. 10.17350/HJSE19030000151 |
| Chicago | KARAYEL ARZU Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. Hittite Journal of Science and Engineering 6, no.3 (2019): 223 - 228. 10.17350/HJSE19030000151 |
| MLA | KARAYEL ARZU Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. Hittite Journal of Science and Engineering, vol.6, no.3, 2019, ss.223 - 228. 10.17350/HJSE19030000151 |
| AMA | KARAYEL A Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. Hittite Journal of Science and Engineering. 2019; 6(3): 223 - 228. 10.17350/HJSE19030000151 |
| Vancouver | KARAYEL A Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety. Hittite Journal of Science and Engineering. 2019; 6(3): 223 - 228. 10.17350/HJSE19030000151 |
| IEEE | KARAYEL A "Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety." Hittite Journal of Science and Engineering, 6, ss.223 - 228, 2019. 10.17350/HJSE19030000151 |
| ISNAD | KARAYEL, ARZU. "Computational Insight into Conformational Rearrangement and Intramolecular-H Bond Analysis of Some Calix[4]Arenes Including Acryloyl Moiety". Hittite Journal of Science and Engineering 6/3 (2019), 223-228. https://doi.org/10.17350/HJSE19030000151 |
