Influence of electronic structure of (R)-4-menten-3-one on its restricted rotation and inversion

Year 2023, , 1 - 9, 03.09.2023

Ivan Vakulin , Elvira Latypova , Rifkat Faatovich , Gumer Yusupovich Ishmuratov Guzel Rafailovna Talıpova

https://doi.org/10.33435/tcandtc.1168638

Abstract

In this work we was study correlation between electronic structure of (R)-4-menthen-3-one and restricted transitions between its conformers. By NBO analysis, carried out in ab inition methods, we found special orbital interactions and sterical effects in conformers of (R)-4-menthen-3-one, which explained difficults of inversion and rotation.

Keywords

Terpenoids, configuration determination, NBO, B3LYP/6-311++G(2d,p), MP2/6-311++G(d,p).

References

• [1] I.V. Vakulin, E.R. Latypova, A.A. Rafikova, N.V. Belkina, I.Sh. Yakupov, R.F. Talipov, G.U. Ishmuratov, Quantum chemical investigation of structure and stability conformers (R)-4-menthen-3-one, Journal of the Chinese Chemical Society 68(4) (2021) 551-556.
• [2] E.R. Latypova, R.Ya. Kharisov, I.V. Vakulin, R.F. Talipov, G. Yu. Ishmuratov, The influence of electronic effects of conjugated enons on their reactivity in transformations of ADDN type, Journal of Structural Chemistry 48(1) (2007) 49-53.
• [3] Ed. D. Barton, V.D. Ollis, General Organic Chemistry, Vol.2, Chemistry, Moscow, Russia, 1982, 856.
• [4] G.Yu. Ishmuratov, E.R. Latypova, R.Ya. Kharisov, R.R. Muslukhov, A.V. Bannova, R.F. Talipov, G.A. Tolstikov, (R)-4-mentenone in reactions of 1,2- and 1,4-conjugate and 1,3-dipolar addition, Russian Journal of Organic Chemistry 44(5) (2008) 652-656.
• [5] G.Yu. Ishmuratov, E.R. Latypova, V.S. Tukhvatshin, A.A. Smolnikov, R.F. Talipov, R.R. Muslukhov, N.M. Ishmuratova, Reactions of (R)-4-Menthen-3-one with Aluminum and Boron-Containing Hydrides, Chemistry of Natural Compounds 48(6) (2013) 978-980.
• [6] G.Yu. Ishmuratov, A.V. Bannova, E.R. Latypova, R.R. Muslukhov, V.S. Tukhvatshin, R.F. Talipov, (R)-4-Menten-3-one in reactions of 1,2- and 1,4-addition of magnesium and lithium organic reagents, Khimiya Rastitel/nogo Syr /ya 2 (2013) 73-84.
• [7] R.Ya. Kharisov, E.R. Latypova, R.F. Talipov, R.R. Muslukhov, G.Yu. Ishmuratov, G.A. Tolstikov, (R)-4-Mentenone in the synthesis of optically pure sex pheromone of the peach leafminer moth (Lyonetia clerkella), Russian Chemical Bulletin, International Edition 44(10) (2003) 2267-2269.
• [8] R.Ya. Kharisov, E.R. Latypova, R.F. Talipov, G.Yu. Ishmuratov, G.A. Tolstikov, New approach to the synthesis of(R)-3-methyl-γ-butyrolactone, Chemistry of Natural Compounds 39(5) (2004) 482-483.
• [9] E.R. Latypova, A.V. Bannova, M.A. Shutova, R.R. Muslukhov, R.F. Talipov, G.Y. Ishmuratov, (R)-4-Menten-3-one in the synthesis of optically pure methylbranched insect pheromones, Bulletin of Bashkir University 15(2) (2010) 282-284.
• [10] G.Y. Ishmuratov, E.R. Latypova, A.V. Bannova, R.R. Muslukhov, M.A. Shutovа, E.M. Vyrypaev, R.F. Talipov, (R)-4-Menten-3-one in the synthesis of pure (S)-(+)-hydroprene, Bulletin of Bashkir University 15(1) (2010) 18.
• [11] G.Y. Ishmuratov, E.R. Latypova, A.V. Bannova, R.R. Muslukhov, M.A. Shutovа, R.F. Talipov, (R)-4-menthen-3-one in the synthesis of (3S)-methylundecand (2S) methyldec-1-ylbromides, key synthons for (S,S,S)-diprionylacetate, Chemistry of Natural Compounds 46(3) (2010) 370-372.
• [12] E.R. Latypova, R.F. Talipov, G.Y. Ishmuratov, Ozonolytic transformations of (R)-4-menthene-3-one and its derivatives in direction to low molecular weight bioregulators, Izvestiya Vysshikh Uchebnykh Zavedenii. Khimiya i Khimicheskaya Tekhnologiya, 59(3) (2016) 3-17.
• [13] G.Y. Ishmuratov, E.R. Latypova, R.Y. Kharisov, R.R.Muslukhov, A.V. Bannova, R.F. Talipov, Synthesis and ozonolytic transformation of trans-5-vinylmentone, Bulletin of Bashkir University 12(4) (2007) 12-15.
• [14] G.Y. Ishmuratov, E.R. Latypova, A.V. Bannova, R.Y. Kharisov, R.F. Talipov, Comparative ozonolysis of cyclic α,β-unsaturated enones, Russian Journal of Organic Chemistry 44(1) (2008) 141-142.
• [15] G.Y. Ishmuratov, A.V. Bannova, E.R. Latypova, R.R. Muslukhov, V.S. Tukhvatshin, R.F. Talipov, The relative reactivity of α,β-unsaturated сycloenones in the ozonolysis reaction, Butlerov Messages 30(5) (2012) 71-72.
• [16] G.Y. Ishmuratov, V.S.Tukhvatshin, E.R. Latypova, R.R. Muslukhov, R.F. Talipov, The reaction of (R)-4-menthen-3-on and (1R,3R)-menthen-3-ol with thiols, Butlerov Messages 32(10) (2012) 18-21.
• [17] G.Y. Ishmuratov, E.R. Latypova, R.Y. Kharisov, R.R. Gazetdinov, A.V. Bannova, V.S. Tukhvatshin, R.F. Talipov, Ozonolysis of (R)-4-menten-3-one in directed synthesis of low-molecular bioregulators of insects, Bulletin of Bashkir University 14(1) (2009) 19-26.
• [18] G.Y. Ishmuratov, A.V. Bannova, E.R. Latypova, V.S. Tukhvatshin O.S. Kukovinets, R.R. Muslukhov, G.A. Tolstikov, Transformation of peroxide ozonolysis products of (R)-4-menth-4-en-3-one in the presence of nitrogen-containing organic compounds, Russian Journal of Organic Chemistry 49(1) (2013) 42-45.
• [19] G.Y. Ishmuratov, R.Y. Kharisov, E.R. Latypova, R.F. Talipov, Natural cyclic α, β-enone monoterpenoids in nucleophilic addition reactions, Chemistry of Natural Compounds 42(4) (2006) 367-388.
• [20] E.R. Latypova, R.F. Talipov, V.S. Tukhvatshin, M.P. Yakovleva, G.Y. Ishmuratov, Transformations of (R)-4-Menthen-3-one and Its Derivatives with the Participation of Hydride-, Nitrogenand Sulphur-Containing Reagents, Chemistry for Sustainable Development 3 (2017) 275-286.
• [21] F. Weinhold and C.R. Landis, Natural Bond Orbitals and extensions of localized bonding concepts, Chemistry Education Research and Practice 2 (2001) 91-104.
• [22] http://classic.chem.msu.su/gran/gamess/index.html
• [23] A.S. Khamidullina, I.V. Vakulin, R.F. Talipov, I.S. Shepelevich, Structure effects of the protonated lincomycin molecule on the mechanism of its complexation wiyh organic compounds, Journal of Structural Chemistry 46 (2005) 985-990.
• [24] D.A. Chuvashov, I.V. Vakulin, F.Z. Galin, R.F. Talipov, A study of the dependence of substituted N, N-acyl defended reto stabilized sulfur yilides structure on their transformations by means of quantum chemistry, Journal of Molecular Structure: THEOCHEM 774(1-3) (2006) 29-32.
• [25] R.I. Makhmutova, I.V. Vakulin, R.F. Talipov, D.A. Chuvashov, E.M. Movsumzade. A study of cobalt and nicel complexes formation with aromatic schiff’s bases, Journal of Molecular Structure: THEOCHEM 819 (2007) 21-25.
• [26] L.A. Curtiss, P.S. Redfern, C. Raghavachari, Gaussian-4 theory using reduced order perturbation theory, Journal of Chemical Physics 126 (2007) 124105.
• [27] K. Kim, C.D. Jordan, Comparison of Density Functional and MP2 Calculations on the Water Monomer and Dimer, Journal of Chemical Physics 98(40) (1994) 10089-10094.
• [28] P.J. Stevens, F.J. Devlin, S.F. Chabalovsky, M.J. Frisch, Ab InitioCalculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields", Journal of Chemical Physics 98(45) (1994) 11623–11627.
• [29] R. Ditchfield, W.J. Hehre, J.A. Pople, Self-Consistent Molecular-Orbital Methods. IX. An Extended Gaussian-Type Basis for Molecular-Orbital Studies of Organic Molecules", Journal of Chemical Physics 54(2) (1971) 724–728.
• [30] Head-Gordon Martin, John A. Plop, Michael J. Frisch, MP2 energy evaluation by direct methods, Chemical Physics Letters 153(6) (1988) 6 503–506.
• [31] Gaussian 03, Revision A.1, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr.T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P. M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
• [32] https://www.chemcraftprog.com
• [33] F. Weinhold and C.R. Landis, Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective, Cambridge University Press, 2005, 760.
• [34] F. Weinhold and C. R. Landis, Discovering Chemistry with Natural Bond. Orbitals, Wiley-VCH, Hoboken NJ, 2012, 319.
• [35] M. Kiani, R. Ghiasi, H. Pasdar and B. Mirza, Theoretical Analysis of Solvent Polarity Effect on the Electronic and Spectroscopic Properties (IR and UV) of the Ni(CO)2(NHC)2 Complex (NHC = 1H-Imidazol-2-ylidene), Russian Journal of Physical Chemistry A 94(2) (2020) 345-351.
• [36] S.H. Saraf and R. Ghiasi, Effect of the Solvent Polarity on the Optical Properties in the (OC)5Cr=(OEt)(Ph) Complex: A Quantum Chemical Study, Russian Journal of Physical Chemistry A 94(5) (2020) 1047-1052.
• [37] J.K. Badenhoop and F. Weinhold, Natural bond orbital analysis of steric interactions, Journal of Chemical Physics 107(1997) 5406-5421.
• [38] J.K. Badenhoop and F. Weinhold, Natural steric analysis: Ab initio van der Waals radii of atoms and ions, Journal of Chemical Physics 107(1997) 5422-5432.