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Influence of the basis set on the calculation of the absolute 13C shieldings of methyl derivatives (CH3X with X = CH3, CN, NH2, NO2, OH, F) with special emphasis in the cases of X = Cl, Br, SH, SeH, and PH2

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Abstract

Within the set of 13 methane derivatives, the best results concerning 13C absolute shieldings were obtained using the GIAO/MP2/6-311++G(d,p) or the GIAO/MP2/aug-cc-pVTZ approximations. An important finding is that the deviations found with the GIAO/B3LYP/6-311++G(d,p) approach appears to be related to the atomic weight of the X atom in CH3X: the higher the atomic weight the larger the deviation.

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References

  1. London F (1937) J Phys Radium 8:397

    Article  CAS  Google Scholar 

  2. Ditchfield R (1974) Mol Phys 27:789

    Article  CAS  Google Scholar 

  3. Kutzelnigg W (1980) ISR J Chem 19:193

    CAS  Google Scholar 

  4. Kaupp M, Bühl M, Malkin VG (2004) Calculation of NMR and EPR Parameters. Theory and Applications. Wiley-VCH, Weinheim

    Book  Google Scholar 

  5. Alkorta I, Blanco F, Elguero J (2010) J Mol Struct Theochem 942:1

    Article  CAS  Google Scholar 

  6. Yap GPA, Claramunt RM, López C, García MA, Pérez-Medina C, Alkorta I, Elguero J (2010) J Mol Struct 965:74

    Article  CAS  Google Scholar 

  7. Avci D, Basoglu A, Atalay Y (2010) Struct Chem 21:213

    Article  CAS  Google Scholar 

  8. Klika KD, Budovská M, Kutschy P (2010) J Fluor Chem 131:467

    Article  CAS  Google Scholar 

  9. Berionni G, Pégot B, Goumont R (2010) Magn Reson Chem 48:101

    CAS  Google Scholar 

  10. Dabbagh HA, Rasti E, Le Grel P, Hocquet A (2010) Tetrahedron 66:2322

    Article  CAS  Google Scholar 

  11. Gauss J (1994) Chem Phys Lett 229:198

    Article  CAS  Google Scholar 

  12. Bühl M, Gauss J, Hofman M, PvR Schleyer (1993) J Am Chem Soc 115:12385

    Article  Google Scholar 

  13. Haase F, Sauer J (1994) J Phys Chem 98:3083

    Article  CAS  Google Scholar 

  14. Enevoldsen T, Oddershede J (1995) Mol Phys 86:235

    Article  CAS  Google Scholar 

  15. Ruud K, Åstrand PO, Taylor PR (2001) J Am Chem Soc 123:4826

    Article  CAS  Google Scholar 

  16. Kupka T (2008) Magn Reson Chem 46:851

    Article  CAS  Google Scholar 

  17. Jain R, Bally T, Rablen PR (2009) J Org Chem 74:4017

    Article  CAS  Google Scholar 

  18. King RB, Heine T, Cormunboeuf C, PvR Schleyer (2004) J Am Chem Soc 126:430

    Article  CAS  Google Scholar 

  19. Okazaki T, Laali KK (2004) J Org Chem 69:510

    Article  CAS  Google Scholar 

  20. Adcock W, Lünsmann D, Peralta JE, Contreras RH (1999) Magn Reson Chem 37:167

    Article  CAS  Google Scholar 

  21. Bühl M, Kaupp M, Malkina OL, Malkin VG (1999) J Comp Chem 20:91

    Article  Google Scholar 

  22. Rege PD, Malkina O, Goroff NS (2002) J Am Chem Soc 124:370

    Article  CAS  Google Scholar 

  23. Glaser R, Chen N, Wu H, Knotts N, Kaupp M (2004) J Am Chem Soc 126:4412

    Article  CAS  Google Scholar 

  24. Autschbach J (2004) In: Kaupp M, Bühl M, Malkin VG (eds) Calculation of NMR and EPR parameters. Theory and applications, Wiley-VCH, Weinheim, p. 227

  25. Ruden TA, Ruud K (2004) In: Kaupp M, Bühl M, Malkin VG (eds) Calculation of NMR and EPR parameters. Theory and applications. Wiley-VCH, Weinheim, p. 153

  26. Rastrelli F, Bagno A (2009) Chem Eur J 15:7990

    Article  CAS  Google Scholar 

  27. Elyashberg M, Blinov K, Smurnyy Y, Churanova T, Williams A (2010) Magn Reson Chem 48:219

    CAS  Google Scholar 

  28. Alkorta I, Elguero J (2010) In: Grunenberg J (ed) Computational spectroscopy. Wiley, New York, in press

  29. Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112:8251

    Article  CAS  Google Scholar 

  30. Barfield M, Fagerness P (1997) J Am Chem Soc 119:8699

    Article  CAS  Google Scholar 

  31. Alkorta I, Elguero J (1998) Struct Chem 9:187

    Article  CAS  Google Scholar 

  32. Kupka T (2009) Magn Reson Chem 47:959

    Article  CAS  Google Scholar 

  33. Jursic BS (1995) Chem Phys Lett 244:263

    Article  CAS  Google Scholar 

  34. Jorge FE, Sagrillo PS, de Oliveira AR (2006) Chem Phys Lett 432:558

    Article  CAS  Google Scholar 

  35. Sarotti AM, Pellegrinet SC (2009) J Org Chem 74:7254

    Article  CAS  Google Scholar 

  36. Kaupp M, Malkina OL, Malkin VG (1997) Chem Phys Lett 265:55

    Article  CAS  Google Scholar 

  37. Malkina OL, Schimmelpfennig B, Kaupp M, Hess BA, Chandra P, Wahlgren U, Malkin VG (1988) Chem Phys Lett 296:93

    Article  Google Scholar 

  38. Kaupp M, Malkina OL, Malkin VG, Pyykkö P (1998) Chem Eur J 4:118

    Article  CAS  Google Scholar 

  39. Kaupp M, Malkina OL (1998) J Chem Phys 108:3648

    Article  CAS  Google Scholar 

  40. Kaupp M, Aubauer C, Engelhardt G, Klapötke TM, Malkina OL (1999) J Chem Phys 110:3897

    Article  CAS  Google Scholar 

  41. Vaara J, Malkina OL, Stoll H, Malkin VG, Kaupp M (2001) J Chem Phys 111:61

    Article  Google Scholar 

  42. Gaussian 03, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adao C, Jaramill, J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian, Inc., Pittsburgh, PA

  43. McIver JW, Komornicki AK (1972) J Am Chem Soc 94:2625

    Article  CAS  Google Scholar 

  44. Becke AD (1988) Phys Rev A 38:3098

    Article  CAS  Google Scholar 

  45. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  46. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  47. Ditchfield R, Hehre WJ, Pople JA (1971) J Chem Phys 54:724

    Article  CAS  Google Scholar 

  48. Frisch MJ, Pople JA, Krishnam R, Binkley JS (1984) J Chem Phys 80:3265

    Article  CAS  Google Scholar 

  49. Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PvR (1983) J Comput Chem 4:294

    Article  CAS  Google Scholar 

  50. Dunning TH Jr (1989) J Chem Phys 90:1007

    Article  CAS  Google Scholar 

  51. Kendall RA, Dunning TH Jr, Harrison RJ (1992) J Chem Phys 96:6769

    Article  Google Scholar 

  52. Woon DE, Dunning TH Jr (1993) J Chem Phys 98:1358

    Article  CAS  Google Scholar 

  53. Møller C, Plesset MS (1934) Phys Rev 1934(46):618

    Article  Google Scholar 

  54. Adamo C, Barone V (1997) Chem Phys Lett 274:242

    Article  CAS  Google Scholar 

  55. Kalinowski HO, Berger S, Braun S (1988) Carbon-13 NMR spectroscopy. John Wiley and Sons, Chichester

  56. Stothers JB (1972) Carbon-13 NMR spectroscopy. Academic Press, New York

    Google Scholar 

  57. Breitmaier E, Voelter W (1978) 13C NMR spectroscopy, 2nd edn. Verlag Chemie, Weinheim

    Google Scholar 

  58. Jameson AK, Jameson CJ (1987) Chem Phys Lett 134:461

    Article  CAS  Google Scholar 

  59. Jackowski K, Raynes WT (1977) Mol Phys 34:465

    Article  CAS  Google Scholar 

  60. Jackowski K (1992) Chem Phys Lett 194:167

    Article  CAS  Google Scholar 

  61. Wielogórska E, Makulski W, Kozminsi W, Jackowski K (2004) J Mol Struct 704:305

    Article  Google Scholar 

  62. Anderson JA, Odom JD (1988) Organometallics 7:267

    Article  CAS  Google Scholar 

  63. Jameson CJ, Jameson AK, Smith NS, Hwang JK, Zia T (1991) J Phys Chem 95:1092

    Google Scholar 

  64. Cheeseman JR, Trucks GW, Keith TA, Frisch MJ (1996) J Chem Phys 104:5497

    Article  CAS  Google Scholar 

  65. Adamo C, Barone V (1998) Chem Phys Lett 298:113

    Article  CAS  Google Scholar 

  66. Wolff SK, Ziegler T (1998) J Chem Phys 109:895

    Article  CAS  Google Scholar 

  67. Alkorta I, Elguero J (2010) Chem Phys Lett 489:35

    Article  CAS  Google Scholar 

  68. Olsson L, Cremer D (1996) J Phys Chem 100:16881

    Google Scholar 

  69. Werstiuk NH, Ma J (1996) Can J Chem 74:875

    Article  CAS  Google Scholar 

  70. Havlin R, McMahon M, Srinivasan R, Le H, Oldfield E (1997) J Phys Chem A 101:8908

    Article  CAS  Google Scholar 

  71. Aliev AE, Coutier-Murias D, Zhou S (2009) J Mol Struct Theochem 893:1

    Article  CAS  Google Scholar 

  72. Silva AMS, Alkorta I, Elguero J, Silva VLM (2001) J Mol Struct 595:1

    Article  CAS  Google Scholar 

  73. Moon S, Case DA (2006) J Comput Chem 27:825

    Article  CAS  Google Scholar 

  74. Emami M, Teimouri A (2009) J Non-Oxide Glass 1:191

    Google Scholar 

  75. Rozhenko AB, Trachevsky VV (2009) Phos Sulfur Silicon Relat Elem 184:1386

    Article  CAS  Google Scholar 

  76. Amini SK, Shaghaghi H, Bain AD, Chabok A, Tafazzoli (2010) Solid State NMR. doi: 10.1016/j.ssnmr.2009.12.001

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Acknowledgments

This work was supported by the Ministerio de Ciencia e Innovación (Project No. CTQ2009-13129-C02-02) and Comunidad Autónoma de Madrid (Project MADRISOLAR, ref. S-0505/PPQ/0225). The authors thank the CTI (CSIC) for allocation of computer time.

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  1. Instituto de Química Médica, CSIC, Juan de la Cierva, 3, 28006, Madrid, Spain

    Ibon Alkorta & José Elguero

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  1. Ibon Alkorta
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Correspondence to Ibon Alkorta.

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Alkorta, I., Elguero, J. Influence of the basis set on the calculation of the absolute 13C shieldings of methyl derivatives (CH3X with X = CH3, CN, NH2, NO2, OH, F) with special emphasis in the cases of X = Cl, Br, SH, SeH, and PH2 . Struct Chem 21, 755–759 (2010). https://doi.org/10.1007/s11224-010-9608-8

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  • DOI: https://doi.org/10.1007/s11224-010-9608-8

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