Abstract
In the current study, we present an intramolecular HB, molecular structure, π-electrons delocalization and vibrational frequencies analysis of 25 possible conformers of 1-(thionitrosomethylene) hydrazine by means of DFT (B3LYP), MP2 methods in conjunction with the 6-311++G** and augmented correlation-consistent polarized-valence triple-zeta basis sets and G2MP2 theoretical level. The influence of the solvent on the stability order of conformers and the strength of intramolecular hydrogen-bonding was considered using the Tomasi’s polarized continuum model. Statistical analyses of quantitative definitions of aromaticity, nucleus independent chemical shift, harmonic oscillator model of aromaticity, aromatic fluctuation index, and the π-electron delocalization parameter (Q) as a geometrical indicator of a local aromaticity, evaluated for this conformers. Further verification of the obtained transition state structures were implemented via intrinsic reaction coordinate (IRC) analysis. Calculations of the 1H NMR chemical shift at GIAO/B3LYP/6-311++G** levels of theory are also presented. The calculated highest occupied molecular orbital (MO) and lowest unoccupied MO energies show that charge transfer occur within the molecule. Hydrogen-bond energies for H-bonded conformers were obtained from Espinosa method and the natural bond orbital theory and the atoms in molecules theory were also applied to get a more precise insight into the nature of such H-bond interactions.
Similar content being viewed by others
References
Schessl HW (1995) In: Othmer K (ed) Encyclopedia of chemical technology, vol 13. Wiley, New York
Golabi SM, Zare HR (1999) J Electroanal Chem 465:168–176
Poso A, Wright Av, Gynther J (1995) Mutat Res 332:63–71
Choudhary G, Hansen H (1998) Chemosphere 37:801–843
Korfhage KM, Ravichandran K, Baldwin RP (1984) Anal Chem 56:1514–1517
Nguyen HP, Seto NOL, Cai Y, Leinala EK, Borisova SN, Palcic MM, Evans SV (2003) Biol J Chem 278:49191–49195
Song Y, Zhang W, Ji H, Zhou Y, Zhu J, Lu J (2001) Zhongguo Yaowu Huaxue Za Zhi 11:311–316
Hobza P, Havlas Z (2000) Chem Rev 100:4253–4264
Raissi H, Yoosefian M, Hajizadeh A, Imampour JS, Karimi M, Farzad F (2012) Bull Chem Soc Jpn 85:87–92
Wysokinski R, Biennko DC, Michalska D, Huyskens TZ (2005) Chem Phys 315:17–26
Raissi H, Yoosefian M, Zamani S, Farzad F (2012) J Sulfur Chem 33:75–85
Krygowski TM, Steüpien BT (2005) Chem Rev 105:3482–3512 (and references therein)
Raissi H, Jalbout AF, Yoosefian M, Fazli M, Nowroozi A, Shahini M, Leon A (2010) Int J Quant Chem 110:821–830
Lammermann A, Szatmari I, Fulop F, Kleinpeter E (2009) J Phys Chem A 113:6197–6205
Raissi H, Yoosefian M, Mollania F, Farzad F, Nowroozi AR, Loghmaninejad D (2011) Comput Theor Chem 966:299–305
Raissi H, Yoosefian M, Mollania F (2012) Int J Quant Chem 112:2782–2786
Raissi H, Yoosefian M, Khoshkhou SJ (2012) Comput Theor Chem 983:1–6
Koch U, Popelier PLA (1995) J Phys Chem 99:9747–9754
Gilli G, Bellucci F, Ferretti V, Bertolasi V (1989) J Am Chem Soc 111:1023–1028
Bertolasi V, Gilli P, Ferretti V, Gilli G (1991) J Am Chem Soc 113:4917–4925
Gilli P, Bertolasi V, Pretto L, Ferretti V, Gilli G (2004) J Am Chem Soc 126:3845–3855
Espinosa E, Molins E (2000) J Chem Phys 113:5686–5694
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann JRE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, revision A.7. Gaussian, Inc, Pittsburgh
Becke AD (1993) J Chem Phys 98:5648–5652
Møller C, Plesset MS (1934) Phys Rev 46:618–622
Kendall RA, Dunning TH, Harrison RJ (1992) J Chem Phys 96:6796–6806
Bader RFW (1998) J Phys Chem A 102:7314–7323
Glendening DE, Reed AE, Carpenter JE, Weinhold F (1996) NBO, Version 3.1. Gaussian, Inc., Pittsburgh
Wendt M, Weinhold F (2001) NBOView 1.0. Theoretical Chemistry Institute, University of Wisconsin, Madison
Tomasi J, Cammi R, Mennucci B, Cappelli C, Corni S (2002) Phys Chem Chem Phys 4:5697–5712
Cyranski MK, Krygowski TM, Katritzky AL, Schleyer PvR (2002) J Org Chem 67:1333–1338
Mrozek A, Karolak-Wojciechowska J, Amiel P, Barbe J (2000) J Mol Struct 524:159–167
Poater J, Duran M, Sola M, Silvi B (2005) Chem Rev 105:3911–3947
Matito E, Durán M, Solà M (2005) J Chem Phys 122:014109–014117
Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112:8251–8260
Krygowski TM, Cyranski MK (2001) Chem Rev 101:1385–1419
Grabowski SJ (2007) J Mol Struct (THEOCHEM) 811:61–67
Durig JR, Little TS, Gounev TK, Gardner JK, Sullivan JF (1996) J Mol Struct 375:83–94
Eliel EL, Wilen SH (1994) Stereochemistry of organic compounds. Wiley, New York
Kemp JD, Pitzer KS (1936) J Chem Phys 4:749–753
Pitzer KS (1952) Discuss Faraday Soc 10:66–93
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Raissi, H., Khanmohammadi, A., Yoosefian, M. et al. Ab initio and DFT studies on 1-(thionitrosomethylene) hydrazine: conformers, energies, and intramolecular hydrogen-bond strength. Struct Chem 24, 1121–1133 (2013). https://doi.org/10.1007/s11224-012-0144-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-012-0144-6