Abstract
The intramolecular hydrogen bond, molecular structure, π electrons delocalization, and vibrational frequencies in 1-(2-iminoethylidene) silan amine and its derivatives have been investigated by means of density functional method with 6-311++G** basis set, in gas phase, water, and carbon tetrachloride solutions. The obtained results showed that the hydrogen bond strength is mainly governed by resonance variations inside the chelate ring induced by the substituent groups. Furthermore, the topological properties of the electron density distributions for N–H···N intramolecular hydrogen bond were analyzed in terms of the Bader's theory of atoms in molecules. On the other hand, the aromaticity of the ring formed is measured using several well-established indices of aromaticity such as nucleus-independent chemical shift, harmonic oscillator models of the aromaticity, para-delocalization index, average two-center indices, aromatic fluctuation index, and π-fluctuation aromatic index. Natural population analysis data, the electron density and Laplacian properties, as well as γ(NH) and ν(NH) were further used for estimation of the hydrogen bonding interactions and the forces driving their formation.
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Jeffrey G, Saenger W (1991) Hydrogen bonding in biochemical structures. Springer, Heidelberg
Desiraju GR (1997) Chem Commun 2:1475–1482
Kirchner B (2007) Phys Rep 440:1–111
Gilli G, Gilli P (2000) J Mol Struct 552:1–15
Palusiak M, Janowska I, Zakrzewski J, Grabowski SJ (2005) Acta Crystallogr C61:m55–m57
Gilli G, Bellucci F, Ferretti V, Bertolasi V (1989) J Am Chem Soc 111:1023–1028
Cyranski MK, Krygowski TM, Katritzky AL, Schleyer PvR (2002) J Org Chem 67:1333–1338
Kuznetsov A, Boldyrev AI, Wang X, Li LS (2002) J Am Chem Soc 124:11791–11801
Alexandrova AN, Boldyrev AI (2003) J Phys Chem A 107:554–560
Matito E, Durán M, Solà M (2005) J Chem Phys 122:014109–014117
Krygowski TM, Cyranski MK, Czarnocki Z, Hafelinger G, Katritzky AR (2000) Tetrahedron 56:1783–1796
Lazzeretti P (2000) Progr Nucl Magn Res Spectr 36:1–88
Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 13:3839–3842
Bernstein HJ, Schneider WG, Pople JA (1956) Proc R Soc London A 236:515–528
Chesnut DB, Bartolotti L (2000) Chem Phys 253:1–11
Poater J, Duran M, Solà M, Silvi B (2005) Chem Rev 105:3911–3947
Baughcum SL, Duerst RW, Rowe WF, Smith Z, Wilson EB (1981) J Am Chem Soc 103:6296–6303
Rowe WF, Duerst RW, Wilson EB (1976) J Am Chem Soc 98:4021–4023
Baughcum SL, Smith Z, Wilson EB, Duerst RW (1984) J Am Chem Soc 106:2260–2265
Turner P, Baughcum SL, Coy SL, Smith Z (1984) J Am Chem Soc 106:2265–2267
Srinivasan R, Feenstra JS, Park ST, Xu S, Zewail AH (2004) J Am Chem Soc 126:2266–2267
Lowrey AH, George C, Dantonio P, Karle J (1971) J Am Chem Soc 93:6399–6403
Egan W, Gunnarsson G, Bull TE, Forsen S (1977) J Am Chem Soc 99:4568–4572
Firth DW, Barbara PF, Trommsdorff HP (1989) Chem Phys 136:349–360
Firth DW, Beyer K, Dvorak MA, Reeve SW, Grushow A, Leopold KR (1991) J Chem Phys 94:1812–1819
Baba T, Tanaka T, Morino I, Yamada KM, Tanaka K (1999) J Chem Phys 110:4131–4133
Seliskar CJ, Hoffmann RE (1982) J Mol Spectrosc 96:146–155
Smith Z, Wilson EB, Duerst RW (1983) Spectrochim Acta A 39:1117–1129
Chiavassa T, Roubin P, Pizzala L, Verlaque P, Allouche A, Marinelli F (1992) J Phys Chem 96:10659–10665
Caminati W, Grabow JU (2006) J Am Chem Soc 128:854–857
Iijima K, Ohnogi A, Shibata S (1987) J Mol Struct 156:111–118
Frisch MJ, Scheiner AC, Schaefer HF, Binkley JS (1985) J Chem Phys 82:4194–4198
Binkley JS, Frisch MJ, Schaefer HF (1986) Chem Phys Lett 126:1–3
Bicerano J, Schaefer HF, Miller WH (1983) J Am Chem Soc 105:2550–2553
Mil’nikov GV, Yagi K, Taketsugu T, Nakamura H, Hirao K (2003) J Chem Phys 119:10–13
Wang Y, Braams BJ, Bowman JM, Carter S, Tew DP (2008) J Chem Phys 128:224314–224323
Belot JA, Clark J, Cowan JA, Harbison GS, Kolesnikov AI, Kye YS, Schultz AJ, Silvernail C, Zhao XG (2004) J Phys Chem B 108:6922–6926
Delchev VB (2004) Monatsh Chem 135:371–384
Buemi G (2002) Chem Phys 277:241–256
Buemi G, Zuccarello F (2004) Chem Phys 306:115–129
Sebban M, Guillard J, Palmas P, Poullain D (2005) Magn Reson Chem 43:563–566
Madsen GKH, Wilson C, Nymand TM, McIntyre GJ, Larsen FK (1999) J Phys Chem A 103:8684–8690
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, Tomasi J, 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
Bader RFW, Streitwieser A, Neuhaus A, Laidig KE, Speers P (1996) J Am Chem Soc 118:4959–4965
Carrol MT, Chang C, Bader RFW (1988) Mol Phys 63:387–405
Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112:8251–8260
Glendening ED, Reed AE, Carpenter JE, Weinhold F (1992) NBO, version 3.1. Gaussian, Inc., Pittsburgh
Wendt M, Weinhold F (2001) NBOView 1.0. Theoretical Chemistry Institute, University of Wisconsin, Madison
Kuznetsov X, Li AE, Zhang HF, Boldyrev AI, Wang LS (2001) Science 291:859–861
Jimenez-Halla JOC, Matito E, Robles J, Sola M (2006) J Organomet Chem 691:4359–4366
Chi XX, Chen XJ, Yuan ZS (2005) J Mol Struct (Theochem) 732:149–153
Lazzeretti P (2004) Phys Chem Chem Phys 6:217–223
Martin NH, Loveless DM, Main KL, Wade DC (2006) J Mol Graph Model 25:389–395
Fulton RL (1993) J Phys Chem 97:7516–7529
Bultinck P, Ponec R, Van Damme S (2005) J Phys Org Chem 18:706–718
Kurkovskaya LN, Shapet’ko NN, Kogan VA, Osipov OA, Zhuchenko TA (1975) Theor Exp Chem 9:203–205
Raissi H, Yoosefian M, Mollania F, Farzad F, Nowroozi AR, Loghmaninejad DJ (2011) Comput Theor Chem 966:299–305
Espinosa E, Molins E, Lecomte C (1998) Chem Phys Lett 285:703–706
Koch U, Popelier P (1995) J Phys Chem 99:9747–9754
Popelier P (2000) Atoms in molecules. An introduction. Prentice-Hall, Pearson Education Limited, Englewood Cliffs
Raissi H, Jalbout AF, Nasseri MA, Yoosefian M, Ghassi H, Hameed A (2008) Int J Quant Chem 108:1444–1451
Hansch C, Leo A, Taft RW (1991) Chem Rev 97:165–195
Onsager L (1936) J Am Chem Soc 58:1486–1493
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Raissi, H., Yoosefian, M., Mollania, F. et al. Electronic structures, intramolecular interactions, and aromaticity of substituted 1-(2-iminoethylidene) silan amine: a density functional study. Struct Chem 24, 123–137 (2013). https://doi.org/10.1007/s11224-012-0038-7
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DOI: https://doi.org/10.1007/s11224-012-0038-7