Abstract.
We have recently developed a new class IV charge model for calculating partial atomic charges in molecules. The new model, called charge model 3 (CM3), was parameterized for calculations on molecules containing H, Li, C, N, O, F, Si, S, P, Cl, and Br by Hartree–Fock theory and by hybrid density functional theory (HDFT) based on the modified Perdew–Wang density functional with several basis sets. In the present article, we extend CM3 for calculating partial atomic charges by Hartree–Fock theory with the economical but well balanced MIDI! basis set. Then, using a test set of accurate dipole moments for molecules containing nitramine functional groups (which include many high-energy materials), we demonstrate the utility of several parameters designed to improve the charges in molecules containing both N and O atoms. We also show that one of our most recently developed CM3 models that is designed for use with wave functions calculated at the mPWXPW91/MIDI! level of theory (where X denotes a variable percentage of Hartree–Fock exchange) gives accurate charge distributions in nitramines without additional parameters for N and O. To demonstrate the reliability of partial atomic charges calculated with CM3, we use these atomic charges to calculate polarization free energies for several nitramines, including the commonly used explosives 1,3,5-trinitro-s-triazine (RDX) and 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane (HNIW), in nitromethane. These polarization energies are large and negative, indicating that electrostatic interactions between the charge distribution of the molecule and the solvent make a large contribution to the free energy of solvation of nitramines. By extension, the same conclusion should apply to solid-state condensation. Also, in contrast to some other charge models, CM3 yields atomic charges that are relatively insensitive to the presence of buried atoms and small conformational changes in the molecule, as well as to the level of treatment of electron correlation. This type of charge model should be useful in the future development of solvation models and force fields designed to estimate intramolecular interactions of nitramines in the condensed phase.
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References
Cioslowski J (1998) In: Schleyer PvR, Allinger NL, Clark T, Gasteiger J, Kollman PA, Schaefer III HF (eds) Encyclopedia of computational chemistry, vol 5. Wiley, New York, p 892
King WT, Mast GB, Blanchette PP (1971) J Chem Phys 56:4440
Coppens P (1992) Annu Rev Phys Chem 43:663
Person WB, Newton JH (1974) J Chem Phys 61:1040
King WT, Mast GB (1976) J Phys Chem 80:2521
Jolly WL, Perry WB (1973) J Am Chem Soc 95:5442
Jolly WL, Perry WB (1974) Inorg Chem 13:2686
Wiberg KB, Wendoloski J (1978) J Am Chem Soc 100:723
Cioslowski J (1989) J Am Chem Soc 111:8333
Cioslowski J, Hay PJ, Ritchie JP (1990) J Phys Chem 94:148
Gimarc BM, Ott JJ (1986) J Am Chem Soc 108:4298
Gimarc BM, Ott JJ (1986) J Am Chem Soc 108:4303
Bonchev D, Kier L (1992) J Math Chem 9:75
Galvez J, Garcia R, Salabert MT, Soler R (1994) J Chem Inf Comput Sci 34:520
Gasteiger J, Marsili M (1980) Tetrahedron 36:3219
Marsili M, Gasteiger J (1980) Croat Chem Acta 53:601
Moriter WJ, Van Genechten K, Gasteiger J (1985) J Am Chem Soc 107:829
Sanderson RT (1983) J Am Chem Soc 105:2259
Abraham RJ, Griffiths L, Loftus P (1982) J Comput Chem 3: 407
Abraham RJ, Smith PE (1987) J Comput Chem 9:288
Mullay J (1985) J Am Chem Soc 108:1770
Mullay J (1988) J Comput Chem 9:764
Mullay J (1991) J Comput Chem 12:369
No KT, Grant JA, Scherega HA (1990) J Phys Chem 94:4732
No KT, Grant JA, Jhon MS, Scherega HA (1990) J Phys Chem 94:4740
Rappé AK, Goddard III WA (1991) J Phys Chem 95:3358
Oliferenko AA, Palyulin VA, Pisarev SA, Neiman AV, Zefirov NS (2001) J Phys Org Chem 14:355
De Proft F, Van Alsenoy C, Peeters A, Langenaeker W, Geerlings P (2002) J Comput Chem 23:1198
Bultinck P, Langenaeker W, Lahorte P, De Proft F, Van Alsenoy C, Tollenaere JP (2002) J Phys Chem A 106:7895
Bultinck P, Langenaeker W, Carbo-Dorca R, Tollenaere JP (2003) J Chem Inf Comput Sci 43:422
Mulliken RS (1935) J Chem Phys 3:564
Mulliken RS (1955) J Chem Phys 23:1833
Mulliken RS (1962) J Chem Phys 36:3428
Löwdin P-O (1950) J Chem Phys 18:365
Thompson JD, Winget P, Truhlar DG (2001) Phys Chem Comm 4:72. DOI: 10.1039/b105076c
Cusachs LC, Politzer P (1968) Chem Phys Lett 1:529
Stout EW, Politzer P (1968) Theor Chim Acta 12:379
Politzer P, Harris RR (1970) J Am Chem Soc 92:6451
Politzer P (1971) Theor Chim Acta 23:203
Politzer P, Mulliken RS (1971) J Chem Phys 55:5135
Politzer P, Reggio PH (1972) J Am Chem Soc 94:8308
Politzer P, Politzer A (1973) J Am Chem Soc 95:5450
Rousseau B, Peeters A, Van Alsenoy C (2001) THEOCHEM 538: 235
Golebiewski A, Rzescowska E (1974) Acta Phys Pol 45:563
Baker J (1985) Theor Chim Acta 68:221
Kar T, Sannigrahi AB, Mukherjee DC (1987) THEOCHEM 153:93
Reed AE, Weinstock RB, Weinhold F (1985) J Chem Phys 83: 735
Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899
Bader RFW, Larouche A, Gatti C, Carroll MT, MacDougal PJ, Wiberg KB (1987) J Chem Phys 87:1142
Coulson CA, Redei LB, Stocker D (1962) Proc R Soc London Ser A 270:357
Popelier PLA (2001) Theor Chem Acc 105:393
Schwartz ME, Coulson CA, Allen LC (1970) J Am Chem Soc 92: 447
Hirshfeld FL (1977) Theor Chim Acta 44:129
Smit PH, Derissen JL, Van Duijneveldt (1979) Mol Phys 37: 521
Kollman PA (1977) J Am Chem Soc 99:4875
Momany FA (1978) J Phys Chem 86:592
Cox SR, Williams DE (1981) J Comput Chem 2:304
Singh UC, Kollman PA (1984) J Comput Chem 5:129
Weiner SJ, Kollman PA, Case DA, Singh UC, Ghio C, Alagona G, Profeta SJ, Weiner P (1984) J Am Chem Soc 106:765
Weiner SJ, Kollman PA, Nguyen DT, Case DA (1986) J Comput Chem 7:230
Chirlian LE, Francl MM (1987) J Comput Chem 8:894
Francl MM, Carey C, Chirlian LE, Gange DM (1996) J Comput Chem 17:367
Francl MM, Chirlian LE (2000) In: Lipkowitz KB, Boyd DB (eds) Reviews in computational chemistry, vol 14. Wiley, New York, p 1
Wiberg KB, Rablen PR (1993) J Comput Chem 14:1504
Breneman CM, Wiberg KB (1990) J Comput Chem 11:361
Besler BH, Merz KM, Kollman PA (1990) J Comput Chem 11:431
Merz KM (1992) J Comput Chem 13:749
Westbrook JD, Levy RM, Krogh-Jesperson K (1992) J Comput Chem 13:979
Montagani R, Tomasi J (1993) THEOCHEM 279:131
Beck B, Clark T, Glen RC (1997) J Comput Chem 18:744
Bayly CI, Cieplak P, Cornell W, Kollman PA (1993) J Phys Chem 97:10629
Sigfridsson E, Ryde U (1998) J Comput Chem 19:377
Storer JW, Giesen DJ, Cramer CJ, Truhlar DG (1995) J Comput-Aid Mol Des 9:87
Li J, Zhu T, Cramer CJ, Truhlar DG (1998) J Phys Chem A 102:1820
Li J, Williams B, Cramer CJ, Truhlar DG (1999) J Chem Phys 110:724
Winget P, Thompson DJ, Xidos JD, Cramer CJ, Truhlar DG (2002) J Phys Chem A 106:10707
Thompson DJ, Cramer CJ, Truhlar DG (2003) J Comput Chem 24: 1291
Brom JM, Schmitz BJ, Thompson JD, Cramer CJ, Truhlar DG (2003) J Phys Chem A 107:6483
Kalinowski JA, Lesyng B, Thompson JD, Cramer CJ, Truhlar DG (2004) J Phys Chem A 108:2545
Sanderson RT (1976) Chemical bonds and chemical energy. Academic, New York
Politzer P, Weinstein H (1979) J Chem Phys 71:4218
Sorescu DC, Rice BM, Thompson DL (1997) J Phys Chem B 101: 798
Sorescu DC, Rice BM, Thompson DL (1998) J Phys Chem B 102: 948
Sorescu DC, Rice BM, Thompson DL (1998) J Phys Chem B 102: 6692
Sorescu DC, Rice BM, Thompson DL (1999) J Phys Chem A 103: 989
Sorescu DC, Boatz JA, Thompson DL (2001) J Phys Chem A 105: 5010
Smith GD, Bharadwaj RK, Bedrov D, Ayyagari (1999) J Phys Chem B 103:705
Lynch BJ, Zhao Y, Truhlar DG (2003) J Phys Chem A 107:1384
Easton RE, Giesen DJ, Welch A, Cramer CJ, Truhlar DG (1996) Theor Chim Acta 93:281
Li J, Cramer CJ, Truhlar DG (1998) Theor Chim Acta 99:192
Thompson JD, Winget P, Truhlar DG (2001) Phys Chem Comm. DOI: 10.1039/b105076c
Adamo C, Barone V (1998) J Chem Phys 108:664
Mayer I (1983) Chem Phys Lett 97:270
Mayer I (1985) Chem Phys Lett 117:396
Mayer I (1986) Int J Quantum Chem 29:73
Fast PL, Sanchez ML, Truhlar DG (1999) Chem Phys Lett 306: 407
Curtiss LA, Redfern PC, Raghavachari K, Rassolov V, Pople JA (1999) J Chem Phys 110:4703
Krishnan R, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650
Frisch MJ, Pople JA, Binkley JS (1984) J Chem Phys 80:3265
Woon DE, Dunning Jr. TH (1993) J Chem Phys 98:1358
Stolevik R, Rademacher P (1969) Acta Chem Scand 23:672
Krebs B, Mandt J (1979) Acta Crystallogr B35:402
Sumpter BG, Thompson DL (1988) J Chem Phys 88:6889
Politzer P, Sukumar N, Jayasuriya K, Ranganathan S (1988) J Am Chem Soc 110:3425
Habibollahzadeh D, Murray JS, Redfern PC, Politzer P (1991) J Phys Chem 95:7703
Kohno Y, Maekawa K, Tsuchioka T, Hashizume T, Imamura A (1993) Chem Phys Lett 214:603
Roszak SJ (1994) Mol Struct 304:269
Khaikin LS, Grikina OE, Vilkov LV, Palafox AM, Boggs JE (1993) J Struct Chem 34:2
Khaikin LS, Grikina OE, Vilkov LV, Boggs JE (1993) J Struct Chem 34:9
Harris JN, Lammerstsma K (1997) J Phys Chem A 101:1370
Johnson MA, Truong TN (1999) J Phys Chem A 103:8840
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr. JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalamani G, Rega N, Petersson GA, Nagatsuji 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, Adamo C, Jaramillo 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 and Pople JA (2003) Gaussian 03, revision A.1. Gaussian, Pittsburgh
Xidos JD, Li J, Thompson JD, Hawkins GD, Winget PD, Zhu T, Rinaldi D, Liotard DA, Cramer CJ, Truhlar DG (2003) MN-GSM, version 3.1. University of Minnesota, Minneapolis
NAG Fortran 90 Library, 4th edn. (2000) The Numerical Algorithms Group, Inc., Oxford
Tyler JK (1963) J Mol Spectrosc 11:39
Hunter EC, Partington JR (1933) J Chem Soc 309
George MV, Wright G (1958) J Am Chem Soc 80:1200
Choi CS, Prince E (1972) Acta Crystallogr B28:2857
Shishkov IF, Vilkov LV, Kolontis M, Rozsondai B (1991) Struct Chem 2:57
Karpwicz RJ, Brill TB (1984) J Phys Chem 88:348
Filhol A, Clement C, Forel M-T, Paviot J, Rey-Lafon M, Richoux G, Trinquecoste C, Cherville J (1971) J Phys Chem 75:2056
Nielson AT, Chafin AP, Christian SL, Moore DW, Nadler MP, Nissan RA, Vanderah DJ (1998) Tetrahedron 54:11793
Lide DR (ed) (2000) CRC handbook of chemistry and physics, 80th edn. CRC Press, Boca Raton
Stark B (1974) In: Hellwege K-H, Hellwege AM (eds) Molecular constants from microwave spectroscopy, Landolt-Börnstein, new series, group II, vol 6. Springer, Berlin Heidelberg, New York, p 261
Nelson RD, Lide DR, Maryott AA (1967) Natl stand ref dat ser, United States National Bureau of Standards NSRDS-NBS 10. Washington
Velnio B, Cané E, Trombetti A, Corbelli G (1992) J Mol Spectrosc 155:1
Velnio B, Cané E, Gagliardi L, Trombetti A, Caminati W (1993) J Mol Spectrosc 161:136
Krugh WD, Gold LP (1974) J Mol Spectrosc 49:423
McClellan AL (1963) Tables of experimental dipole moments. WH Freeman, San Francisco
Stark B (1967) In: Hellwege K-H, Hellwege AM (eds) Molecular constants from microwave spectroscopy, Landolt-Börnstein, new series, group II, vol 4. Springer, Berlin Heidelberg, New York, p 136
Stark B (1982) In: Hellwege K-H, Hellwege AM (eds) Molecular constants from microwave spectroscopy, Landolt-Börnstein, new series, group II, vol 14a. Springer, Berlin Heidelberg New York, p 261
Caminati W, Velnio B, Danieli R (1993) J Mol Spectrosc 161:208
Becke AD (1997) J Chem Phys 107:8554
Becke AD (1988) Phys Rev A 38:3098
Lee C, Yang W, Parr RG (1987) Phys Rev B 37:785
Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) J Phys Chem 98:11623
Becke AD (1993) J Chem Phys 98:5648
Hamprecht FA, Cohen AJ, Tozer DJ, Handy NC (1998) J Chem Phys 109:6264
Wilson PJ, Bradley TJ, Tozer DJ (2001) J Chem Phys 115: 9233
Schmider HL, Becke AD (1998) J Chem Phys 108:9264
Thompson JD, Cramer CJ, Truhlar DG (2004) J Phys Chem A 108:6532
Hoijtink GJ, Boer ED, Meij PHvD, Weijland WP (1956) Recl Trav Chim Pays-Bas 75:487
Peradejori F (1963) Cah Phys 17:393
Tucker SC, Truhlar DG (1989) Chem Phys Lett 157:164
Still WC, Tempczyk A, Hawley RC, Hendrickson T (1990) J Am Chem Soc 112:6127
Winget P, Dolney DM, Giesen DJ, Cramer CJ, Truhlar DG (1999) Minnesota solvent descriptor database. http://comp.chem.umn.edu/solvation/mnsddb.pdf
Thompson JD, Cramer CJ, Truhlar DG (2003) J Chem Phys 119:1661
Walsh ME, Jenkins TF, Thorne PG (1995) J Energ Mater 13: 357
Syracuse research corporation (1994) Physical/chemical property database (PHYSPROP), SRC Environmental Science Center, Syracuse
Leo AJ (1994) Masterfile from MedChem Software, BioByte Corp., Claremont
Ben-Naim A (1987) Solvation thermodynamics. Plenum, New York
Tapia O (1980) In: Daudel R, Pullman A, Salem L, Viellard A (eds) Quantum theory of chemical reactions. Reidel, Dordrecht, p 25
Zhu T, Li J, Hawkins GD, Cramer CJ, Truhlar DG (1998) J Chem Phys 109:9117
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Kelly, C., Cramer, C. & Truhlar, D. Accurate partial atomic charges for high-energy molecules using class IV charge models with the MIDI! basis set. Theor Chem Acc 113, 133–151 (2005). https://doi.org/10.1007/s00214-004-0624-x
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DOI: https://doi.org/10.1007/s00214-004-0624-x