Abstract
Solid-state nuclear magnetic resonance (NMR) parameters of 17O, 14N/15N, and 2H/1H nuclei were evaluated in two available neutron crystalline structures of N-methylacetamide (NMA) at 250 and 276 K, NMA-I and NMA-II, respectively. Density functional theory calculations were performed by B3LYP method and 6-311++G** and IGLO-II type basis sets to calculate the electric field gradient (EFG) and chemical shielding (CS) tensors at the sites of mentioned nuclei. In order to investigate hydrogen bonds (HBs) effects on NMR tensors, calculations were performed on four-model systems of NMA: an optimized isolated gas-phase, crystalline monomers, crystalline dimers, and crystalline trimers. Comparing the calculated results reveal the influence of N–H···O=C and C–H···O=C HB types on the NMR tensors which are observable by the evaluated parameters including quadrupole coupling constant, C Q, and isotropic CS, σ iso. Furthermore, the results demonstrate more influence of HB on the EFG and CS tensors of NMA at 276 K rather than that of 250 K.
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Whitford D (2005) Proteins: structure and function. Wiley
Bounouar M, Scheurer Ch (2006) Chem Phys 323:87
Woutersen S, Mu Y, Stock G, Hamm P (2001) Chem Phys 266:137
Whitfield TW, Martyna GJ, Allison S, Bates SP (2005) Crain J Chem Phys Lett 414:210
Hiramatsu H, Hamaguchi H (2002) Chem Phys Lett 361:457
Rocha WR, De Almeida KJ, Coutinho K, Canuto S (2001) Chem Phys Lett 345:171
Qian W, Mirkin NG, Krimm S (1999) Chem Phys Lett 315:125
Whitfield TW, Martyna GJ, Allison S, Bates SP, Vass H, Crain J (2006) J Phys Chem B 110:3624
DeCamp MF, DeFlores L, McCracken JM, Tokmakoff A, Kwac K, Cho M (2005) J Phys Chem B 109:11016
Mennucci B, Martínez JM (2005) J Phys Chem B 109:9830
Czarnecki MA; Haufa KZ (2005) J Phys Chem A 109:1015
Weise CF, Weisshaar JC (2003) J Phys Chem B 107:6552
Martínez AG, Vilar ET, Fraile AG, Martínez-Ruiz P (2002) J Phys Chem A 106:4942
Ludwig R, Weinhold F, Farrar TC (1997) J Phys Chem A 101:8861
Das TP, Han EL (1958) Nuclear quadrupole resonance spectroscopy. Academic Press, NY
Bovey FA (1988) Nuclear magnetic resonance spectroscopy. Academic Press, San Diego
Eckert J, Barthes M, Klooster WT, Albinati A, Aznar R, Koetzle TF (2001) J Phys Chem B 105:19
Ida R, Clerk MD, Wu G (2006) J Phys Chem A 110:1065
Mirzaei M, Hadipour NL (2006) J Phys Chem A 110:4833
Becke AD (1993) J Chem Phys 98:5648
Lee C, Yang W, Parr RG (1988) Phys Rev B: Condens Matter 37:785
Frisch MJ et al (1998) Gaussian 98. Revision A7. Gaussian Inc., Pittsburgh, PA
Krishnan R, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650
Clark T, Chandrasekhar J, Schleyer PvR (1983) J Comp Chem 4:294
Kutzelnigg W, Fleischer U, Schindler M (1990) The IGLO-method: ab initio calculation and interpretation of NMR chemical shifts and magnetic susceptibilities, vol 23. Springer-Verlag, Heidelberg
Huzinaga S (1965) J Chem Phys 42:1293
Schindler M, Kutzelnigg W (1983) J Am Chem Soc 105:1360
Fleischer U, Kutzelnigg W, Bleiber A, Sauer J (1993) J Am Chem Soc 115:7833
Mirzaei M, Hadipour NL (2007) Chem Phys Lett 438:304
Fängström T, Lunell S, Kasai PH, Eriksson LA (1998) J Phys Chem A 102:1005
Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112:8251
Drago RS (1992) Physical methods for chemists, 2nd edn. Saunders College Publishing, FL
Pyykkö P (2001) Mol Phys 99:1617
Wasylishen RE, Bryce DL (2002) J Chem Phys 117:10061
Jameson CJ, Mason J (1987) Multinuclear NMR. Plenum Press, NY, p 56
Gobetto R, Nervi C, Valfrè E, Chierotti MR, Braga D, Maini L, Grepioni F, Harris RK, Ghi PY (2005) Chem Mater 17:1457
Xu X-P, Au-Yeung SCF (2000) J Phys Chem B 104:5641
Raymo FM, Bartberger MD, Houk KN, Stoddart JF (2001) J Am Chem Soc 123:9264
Vargas R, Garza J, Friesner RA, Stern H, Hay BP, Dixon DA (2001) J Phys Chem A 105:4963
Wang B, Hinton JF, Pulay P (2003) J Phys Chem A 107:4683
Zhang R, Li H, Lei Y, Han S (2004) J Phys Chem B 108:12596
Gavezzotti A, Filippini G (1994) J Phys Chem A 98:4831
Smirnov SN, Golubev NS, Denisov GS, Benedict H, Schah-Mohammedi P, Limbach H-H (1996) J Am Chem Soc 118:4094
Bordallo HN, Argyriou DN, Barthe`s M, Kalceff W, Rols S, Herwig KW, Fehr C, Juranyi F, Seydel T (2007) J Phys Chem B 111:7725
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The authors gratefully thank the Research Council of Tarbiat Modares University for financial supports.
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Mirzaei, M., Hadipour, N.L. Study of hydrogen bonds in N-methylacetamide by DFT calculations of oxygen, nitrogen, and hydrogen solid-state NMR parameters. Struct Chem 19, 225–232 (2008). https://doi.org/10.1007/s11224-007-9276-5
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DOI: https://doi.org/10.1007/s11224-007-9276-5