Computational investigation of adsorption of Lewisite Warfare Agents on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters
محورهای موضوعی : Journal of NanoanalysisReza Ghiasi 1 , R Emami 2 , M Vasfi 3
1 - East Tehran branch of Islamic azad university
2 - Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran
3 - Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran
کلید واژه: Adsorption, Molecular orbital analysis, B12N12 cluster, Lewisite, Population of conduction electrons,
چکیده مقاله :
This research surveyed the adsorption of Lewisite warfare agent on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters with at the LC-wPBE/ 6-311+G(d,p) level of theory. Adsorption energy values of Lewisite on the nanoclusters were computed, and impact of metal cation on the adsorption was uncovered. Thermodynamics parameters of these responses were computed. Molecular orbital analyses of the B12N12 … Lewisite and M+@B12N12 …. Lewisite systems were explained.Computational examination of adsorption of Lewisite warfare agent on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nano-clusters with at the LC-wPBE/ 6-311+G(d,p) level of theory shown the doped nano-clusters had more propensity to adsorb Lewisite than B12N12 cluster. Appropriation strength decreased with increasing of effective atomic number of metal cation. Lewisite fragment had importance commitment within the frontier orbitals of examined systems. Responses of M+@B12N12… Lewisite complexes arrangement were the more spontaneous and exothermic than B12N12… Lewisite complex. This computational study regarded the interaction between B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters with Lewisite warfare agent at LC-wPBE/ 6-311+G(d,p) level of theory. The structural parameters, frontier orbital energies and thermodynamics parameters were computed. The impact of metal cation on the adsorption was outlined.
This research surveyed the adsorption of Lewisite warfare agent on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters with at the LC-wPBE/ 6-311+G(d,p) level of theory. Adsorption energy values of Lewisite on the nanoclusters were computed, and impact of metal cation on the adsorption was uncovered. Thermodynamics parameters of these responses were computed. Molecular orbital analyses of the B12N12 … Lewisite and M+@B12N12 …. Lewisite systems were explained.Computational examination of adsorption of Lewisite warfare agent on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nano-clusters with at the LC-wPBE/ 6-311+G(d,p) level of theory shown the doped nano-clusters had more propensity to adsorb Lewisite than B12N12 cluster. Appropriation strength decreased with increasing of effective atomic number of metal cation. Lewisite fragment had importance commitment within the frontier orbitals of examined systems. Responses of M+@B12N12… Lewisite complexes arrangement were the more spontaneous and exothermic than B12N12… Lewisite complex. This computational study regarded the interaction between B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters with Lewisite warfare agent at LC-wPBE/ 6-311+G(d,p) level of theory. The structural parameters, frontier orbital energies and thermodynamics parameters were computed. The impact of metal cation on the adsorption was outlined.
References:
1. Marrs TC, Maynard RL, Sidell FR, Chemical Warfare Agents: Toxicology and Treatment. Wiley: New York, 1996.
2. Green SJ, Price TWI, The Chlorovinylchloroarsines. J. Chem. Soc. Trans. , 1921; 119: 448−453.
3. Webb JL, Arsenicals; Enzyme and Metabolic Inhibitors. Academic Press: New York, 1966; Vol. 3.
4. Szekeres LI, Gyurcsik B, Kiss T, Kele Z, Jancsó A, Interaction of Arsenous Acid with the Dithiol-Type Chelator British Anti-Lewisite (BAL): Structure and Stability of Species Formed in an Unexpectedly Complex System. Inorganic Chemistry, 2018; 57: 7191-7200.
5. Sahu C, Pakhira S, Sen K, Das AK, A Computational Study of Detoxification of Lewisite Warfare Agents by British Anti-lewisite: Catalytic Effects of Water and Ammonia on Reaction Mechanism and Kinetics. J. Phys. Chem. A, 2013; 117: 3496−3506.
6. Strout DL, Structure and Stability of Boron Nitrides: Isomers of B12N12. J. Phys. Chem. A 2000; 104: 3364–3366.
7. Wang R, Zhang D, Liu C, Theoretical prediction of a novel inorganic fullerene-like family of silicon–carbon materials. Chem. Phys. Lett., 2005; 411: 333-338.
8. Bertolus B, Finocchi F, Millie P, Investigating bonding in small silicon-carbon clusters: exploration of the potential energy surfaces of Si3C4, Si4C3, and Si4C4 using ab initio molecular dynamics. J. Chem. Phys., 2004; 120: 4333-4343.
9. Fu C-C, Weissmann M, Machado M, Ordejón P, Ab initio study of silicon-multisubstituted neutral and charged fullerenes. Phys. Rev. B 2001; 63: 85411.
10. Kandalam AK, Blanco MA, Pandey R, Theoretical Study of Structural and Vibrational Properties of Al3N3, Ga3N3, and In3N3. J. Phys. Chem. B, 2001; 105: 6080–6084.
11. Tahmasebi ESE, Biglari Z, Theoretical assessment of the electro-optical features of the group III nitrides (B12N12, Al12N12 and Ga12N12) and group IV carbides (C24, Si12C12 and Ge12C12) nanoclusters encapsulated with alkali metals (Li, Na and K). Appl. Surf. Sci., 2016; 363: 197–208.
12. Zhang QWF, Wang X, Liu N, Yang J, Hu Y, Yu L, Hu Z, Zhu J, 6-Fold-Symmetrical AlN Hierarchical Nanostructures: Synthesis and Field-Emission Properties. J. Phys. Chem. C, 2009; 113: 4053–4058.
13. Wu H-S, Zhang F-Q, Xu X-H, Zhang C-J, Jiao H, Geometric and Energetic Aspects of Aluminum Nitride Cages. J. Phys. Chem. A, 2003; 107: 204–209.
14. Wu H, Fan X, Kuo J-L, Metal free hydrogenation reaction on carbon doped boron nitride fullerene: A DFT study on the kinetic issue. Int. J. Hydrogen Energy, 2012; 37: 14336–14342.
15. Kim KK, Hsu A, Jia X, Kim SM, Shi Y, Hofmann M, Nezich D, Rodriguez-Nieva JF, Dresselhaus M, Palacios T, Synthesis of monolayer hexagonal boron nitride on Cu foil using chemical vapor deposition. Nano letters, 2011; 12: 161-166.
16. Ciofani G, Genchi GG, Liakos I, Athanassiou A, Dinucci D, Chiellini F, Mattoli V, A simple approach to covalent functionalization of boron nitride nanotubes. Journal of colloid and interface science, 2012; 374: 308-314.
17. Oku T, Nishiwaki A, Narita I, Sci. Technol. Adv. Mater, 2004; 5: 635-.
18. Oku T, Narita I, Nishiwaki A, Mater. Manuf. Process. , 2004; 19:
19. Baei MT, Taghartapeh MR, Lemeski ET, Soltani A, A computational study of adenine, uracil, and cytosine adsorption upon AlN and BN nano-cages. Physica B 2014; 444: 6–13.
20. Rad AS, Ayub K, Adsorption of pyrrole on Al12N12, Al12P12, B12N12, and B12P12 fullerene-like nano-cages; a first principles study. Vacuum 2016; 131: 135-141.
21. Soltani A, Baei MT, Lemeski ET, Shahini M, Sensitivity of BN nano-cages to caffeine and nicotine molecules. Superlattices and Microstructures 2014; 76: 315–325.
22. Vessally E, Esrafili MD, Nurazar R, Nematollahi P, Bekhradnia A, A DFT study on electronic and optical properties of aspirin-functionalized B12N12 fullerene-like nanocluster. Structural Chemistry, 2017; 28: 735–748.
23. S.Onsori, Alipour E, A computational study on the cisplatin drug interaction with boron nitride nanocluster. Journal of Molecular Graphics and Modelling, 2018; 79: 223-229.
24. Soltani A, Sousaraei A, Javan MB, Eskandaric M, Balakheylid H, Electronic and optical properties of 5-AVA-functionalized BN nanoclusters: a DFT study New J. Chem., 2016; 40: 7018-7026.
25. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalman G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, T. Nakajima, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, J. Normand, Raghavachari K, Rendell A, Burant JC, Iyengar SS, J. Tomasi, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford CT, 2009.
26. Krishnan R, Binkley JS, Seeger R, Pople JA, Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys., 1980; 72: 650.
27. McLean AD, Chandler GS, Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18. J. Chem. Phys., 1980; 72: 5639.
28. Curtiss LA, McGrath MP, Blandeau J-P, Davis NE, Binning RC, Radom JL, Extension of Gaussian‐2 theory to molecules containing third‐row atoms Ga–Kr. J. Chem. Phys., 1995; 103: 6104.
29. Vydrov OA, Scuseria GE, Assessment of a long-range corrected hybrid functional. J. Chem. Phys., 2006; 125: 234109.
30. Breneman CM, Wiberg KB, Determining atom-centered monopoles from molecular electrostatic potentials - the need for high sampling density in formamide conformational-analysis. J. Comp. Chem., 1990; 11: 361-373.
31. S. Simon MD, Dannenberg JJ, How does basis set superposition error change the potential surfaces for hydrogen bonded dimers? J. Chem. Phys., 1996; 105: 11024-11031.
Computational investigation of adsorption of Lewisite Warfare Agents on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters
Reza Ghiasi*, Rashin Emami, Maryam Vasfi Sofiyani
Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran
E-mail to: rezaghiasi1353@yahoo.com, rghiasi@iauet.ac.ir
Abstract
This research surveyed the adsorption of Lewisite warfare agent on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters with at the LC-wPBE/ 6-311+G(d,p) level of theory. Adsorption energy values of Lewisite on the nanoclusters were computed, and impact of metal cation on the adsorption was uncovered. Thermodynamics parameters of these responses were computed. Molecular orbital analyses of the B12N12 … Lewisite and M+@B12N12 …. Lewisite systems were explained.
Keywords: B12N12 cluster, Lewisite, Adsorption, Molecular orbital analysis, Population of conduction electrons, Thermodynamics parameters.
Introduction
Genuine health risks are made taking after the contamination of environment by chemical warfare agent (CWA). Among CWAs, trans- 2-chlorovinyldichloroarsine, known as Lewisite (Lew-I), may be a capable rankling chemical warfare operator; the primary generation of this agent dates back to the conclusion of World War I and it cause serious chemical burns of the eyes, skin, and lungs [1]. For obtaining Lewisite, acetylene responds with arsenic trichloride [2]. Trivalent arsenic is poisonous dud to its reactivity with noteworthy organic sulfhydryls [3].In World War II, British Anti-Lewisite, 2,3 dimerceptopropanol (H2DMPA, BAL), was connected as an antidote to the chemical weapon Lewisite, 2-chloroethenyldichloroarsine, the so-called “Dew of Death”. Amazingly, the activity instrument at the molecular level and the coordination property of this conventional medicate towards various arsenicals are hazy. A few research centered on the interaction of arsenous corrosive with the BAL demonstrating the structure and soundness of species made in a suddenly complex system [4]. A research detailed computational examination of detoxification of Lewisite warfare operators by British anti-Lewisite [5]. Nano structures like fullerene empty nano-clusters of components other than carbon were favored due to their uncommon electronic and optical characteristics [6-9]. Group III-V nitrides are among the foremost profitable nano-clusters [10-14]. BN nanoclusters are the isostructural course of carbon bucky balls, arranged by chemical vapor testimony strategy [15]. These particles have been utilized for helpful purposes due to the biocompatibility [16].They are regarded to be challenge for carbon based fullerenes within the following era gadgets. Arrangement of the B12N12 nanocluster was detailed by laser desorption time-of flight mass spectrometry [17, 18]. A few computational examinations almost of intelligent between B12N12 cluster and different molecules were explained [19-24].
This computational study regarded the interaction between B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nanoclusters with Lewisite warfare agent at LC-wPBE/ 6-311+G(d,p) level of theory. The structural parameters, frontier orbital energies and thermodynamics parameters were computed. The impact of metal cation on the adsorption was outlined.
Computational Methods
Optimization and vibrational investigation were performed with Gaussian 09 software package [25]. The standard 6-311+G(d,p) basis set [26-28] were regarded. LC-wPBE functional (a long range-corrected adaptation of wPBE) [29] is the level of theory that most precisely explains the HOMO–LUMO gap. The identities of optimized structures as a vitality least were affirmed by vibrational analysis.
Results and discussion
1. Adsorption Energy Values
The most stable isomer of the adsorbed Lewisite on the B12N12 nano-cluster is displayed in Figure 1. At that point, this isomer is doped with alkaline metal cations. Chosen metal cations are Li+, Na+, and K+. Adsorption vitality values of the Lewisite particle on the M+@B12N12 nano-clusters are recorded in Table 2. The adsorption energy value (DEad) is ordinarily computed as below:
Where, E (cluster) is the vitality of isolate cluster, E (Lewisite) is the energy of the separated Lewisite, and E (cluster…Lewisite) is the energy of Lewisite adsorbed on the cluster surface. E(BSSE) is the basis set superposition errors (BSSE), which was corrected for adsorption vitality [30, 31]. The large negative DEads shows the adsorption of Lewisite particle on the nano-clusters. It can be found, these adsorptions are vivaciously favorable. The adsorption energies shown that the doped nanoclusters have more propensity to adsorb Lewisite than B12N12 cluster. Adoption strength decrease with increasing of atomic number of metal cation.
2. Bond distances
B-C and N-C bond separations of Lewisite…B12N12 and Lewisite…M+@B12N12 nano-clusters frameworks are recorded in Table 1. It can be found, longer B-C and N-C bonds within the Lewisite…M+@B12N12 systems than Lewisite…B12N12 system. B-C bond lengths decrease with increasing of atomic number of metals within the Lewisite…M+@B12N12 systems. In contrast, N-C bond lengths increase with increasing of atomic number of metals within the Lewisite…M+@B12N12 systems.
3. Molecular orbital analysis
The frontier orbitals energy values and the HOMO-LUMO gap values in B12N12 and M+@B12N12 nano-clusters systems are recorded in Table 2. These values uncover, the more stability of frontier orbital within the metal-doped clusters in compared to exclusively cluster. On the other hand, HOMO-LUMO gap values are decreased within the M+@B12N12 systems compared to B12N12 cluster. Plots of frontier orbital in e Lewisite…B12N12 and Lewisite…Li+@B12N12 nano-clusters systems are displayed in Figure 2. It can be observed, significance contribution of Lewisite fragment within the frontier orbitals of these systems. Comparative plots were seen within the Lewisite…Na+@B12N12 and Lewisite…K+@B12N12 systems.
4. Population of conduction electrons
The population of conduction electrons (N) can be calculated with following equation:
In this equation, kB, DEgap, T and A are Boltzmann’s constant, HOMO-LUMO gap energy, temperature and a constanat (in electrons/m3 K3/2). DEgap values regarded as a reasonable parameter for an adsorbent’s affectability to an adsorbate. If DEgap values drop, an exponential increment will happen within the populace of conduction electrons. The electron populace will ordinarily be modified into an electric flag. The magnitude of this signal might be ascribed to the nearness of Lewisite molecule. Hence, B12N12 and M+@B12N12 nanoclusters can recognize the nearness of Lewisite by making an electrical noise.
5. Thermodynamic parameters
Free energy enthalpy and entropy changes (DG, DH and DS, respectively) of B12N12…Lewisite and M+@B12N12… Lewisite complexes formation are computed in the basis of following reactions:
B12N12 + Lewisite ® B12N12… Lewisite; DX =X(B12N12… Lewisite) – X(B12N12) - X(Lewisite); X=G, H, S
M+@B12N12 + Lewisite ® M+@B12N12… Lewisite; DX =X(M+@B12N12… Lewisite) – X(M+@B12N12)-X(Lewisite); X=G, H, S
The computed parameters are recorded in Table 3. The negative DG and DH values of the B12N12… Lewisite and M+@B12N12… Lewisite complexes uncover that the examined responses are spontaneous and exothermic, respectively. The negative DS values of these responses are consistent. Since, arrangement of the one particles after interaction between two molecules diminish entropy of reaction. The more negative values of DG and DH indicate the more spontaneous and exothermic responses of M+@B12N12… Lewisite complexes arrangement than B12N12… Lewisite complex. DG and DH values are diminished with expanding of the nuclear effective charge of M+.
Formation constant values (K) of the arrangement of these complexes are calculated by following formula:
The computed K values are recorded in Table 3. It can be seen, the larger values for M+@B12N12… Lewisite complexes than B12N12… Lewisite complex. These values increment with increasing of the nuclear efficient charge of M+.
Conclusion:
Computational examination of adsorption of Lewisite warfare agent on the B12N12 and M+@B12N12 (M+ = Li+, Na+, K+) nano-clusters with at the LC-wPBE/ 6-311+G(d,p) level of theory shown the doped nano-clusters had more propensity to adsorb Lewisite than B12N12 cluster. Appropriation strength decreased with increasing of effective atomic number of metal cation. Lewisite fragment had importance commitment within the frontier orbitals of examined systems. Responses of M+@B12N12… Lewisite complexes arrangement were the more spontaneous and exothermic than B12N12… Lewisite complex.
References:
1. Marrs TC, Maynard RL, Sidell FR, Chemical Warfare Agents: Toxicology and Treatment. Wiley: New York, 1996.
2. Green SJ, Price TWI, The Chlorovinylchloroarsines. J. Chem. Soc. Trans. , 1921; 119: 448−453.
3. Webb JL, Arsenicals; Enzyme and Metabolic Inhibitors. Academic Press: New York, 1966; Vol. 3.
4. Szekeres LI, Gyurcsik B, Kiss T, Kele Z, Jancsó A, Interaction of Arsenous Acid with the Dithiol-Type Chelator British Anti-Lewisite (BAL): Structure and Stability of Species Formed in an Unexpectedly Complex System. Inorganic Chemistry, 2018; 57: 7191-7200.
5. Sahu C, Pakhira S, Sen K, Das AK, A Computational Study of Detoxification of Lewisite Warfare Agents by British Anti-lewisite: Catalytic Effects of Water and Ammonia on Reaction Mechanism and Kinetics. J. Phys. Chem. A, 2013; 117: 3496−3506.
6. Strout DL, Structure and Stability of Boron Nitrides: Isomers of B12N12. J. Phys. Chem. A 2000; 104: 3364–3366.
7. Wang R, Zhang D, Liu C, Theoretical prediction of a novel inorganic fullerene-like family of silicon–carbon materials. Chem. Phys. Lett., 2005; 411: 333-338.
8. Bertolus B, Finocchi F, Millie P, Investigating bonding in small silicon-carbon clusters: exploration of the potential energy surfaces of Si3C4, Si4C3, and Si4C4 using ab initio molecular dynamics. J. Chem. Phys., 2004; 120: 4333-4343.
9. Fu C-C, Weissmann M, Machado M, Ordejón P, Ab initio study of silicon-multisubstituted neutral and charged fullerenes. Phys. Rev. B 2001; 63: 85411.
10. Kandalam AK, Blanco MA, Pandey R, Theoretical Study of Structural and Vibrational Properties of Al3N3, Ga3N3, and In3N3. J. Phys. Chem. B, 2001; 105: 6080–6084.
11. Tahmasebi ESE, Biglari Z, Theoretical assessment of the electro-optical features of the group III nitrides (B12N12, Al12N12 and Ga12N12) and group IV carbides (C24, Si12C12 and Ge12C12) nanoclusters encapsulated with alkali metals (Li, Na and K). Appl. Surf. Sci., 2016; 363: 197–208.
12. Zhang QWF, Wang X, Liu N, Yang J, Hu Y, Yu L, Hu Z, Zhu J, 6-Fold-Symmetrical AlN Hierarchical Nanostructures: Synthesis and Field-Emission Properties. J. Phys. Chem. C, 2009; 113: 4053–4058.
13. Wu H-S, Zhang F-Q, Xu X-H, Zhang C-J, Jiao H, Geometric and Energetic Aspects of Aluminum Nitride Cages. J. Phys. Chem. A, 2003; 107: 204–209.
14. Wu H, Fan X, Kuo J-L, Metal free hydrogenation reaction on carbon doped boron nitride fullerene: A DFT study on the kinetic issue. Int. J. Hydrogen Energy, 2012; 37: 14336–14342.
15. Kim KK, Hsu A, Jia X, Kim SM, Shi Y, Hofmann M, Nezich D, Rodriguez-Nieva JF, Dresselhaus M, Palacios T, Synthesis of monolayer hexagonal boron nitride on Cu foil using chemical vapor deposition. Nano letters, 2011; 12: 161-166.
16. Ciofani G, Genchi GG, Liakos I, Athanassiou A, Dinucci D, Chiellini F, Mattoli V, A simple approach to covalent functionalization of boron nitride nanotubes. Journal of colloid and interface science, 2012; 374: 308-314.
17. Oku T, Nishiwaki A, Narita I, Sci. Technol. Adv. Mater, 2004; 5: 635-.
18. Oku T, Narita I, Nishiwaki A, Mater. Manuf. Process. , 2004; 19:
19. Baei MT, Taghartapeh MR, Lemeski ET, Soltani A, A computational study of adenine, uracil, and cytosine adsorption upon AlN and BN nano-cages. Physica B 2014; 444: 6–13.
20. Rad AS, Ayub K, Adsorption of pyrrole on Al12N12, Al12P12, B12N12, and B12P12 fullerene-like nano-cages; a first principles study. Vacuum 2016; 131: 135-141.
21. Soltani A, Baei MT, Lemeski ET, Shahini M, Sensitivity of BN nano-cages to caffeine and nicotine molecules. Superlattices and Microstructures 2014; 76: 315–325.
22. Vessally E, Esrafili MD, Nurazar R, Nematollahi P, Bekhradnia A, A DFT study on electronic and optical properties of aspirin-functionalized B12N12 fullerene-like nanocluster. Structural Chemistry, 2017; 28: 735–748.
23. S.Onsori, Alipour E, A computational study on the cisplatin drug interaction with boron nitride nanocluster. Journal of Molecular Graphics and Modelling, 2018; 79: 223-229.
24. Soltani A, Sousaraei A, Javan MB, Eskandaric M, Balakheylid H, Electronic and optical properties of 5-AVA-functionalized BN nanoclusters: a DFT study New J. Chem., 2016; 40: 7018-7026.
25. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalman G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, T. Nakajima, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, J. Normand, Raghavachari K, Rendell A, Burant JC, Iyengar SS, J. Tomasi, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford CT, 2009.
26. Krishnan R, Binkley JS, Seeger R, Pople JA, Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys., 1980; 72: 650.
27. McLean AD, Chandler GS, Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z=11–18. J. Chem. Phys., 1980; 72: 5639.
28. Curtiss LA, McGrath MP, Blandeau J-P, Davis NE, Binning RC, Radom JL, Extension of Gaussian‐2 theory to molecules containing third‐row atoms Ga–Kr. J. Chem. Phys., 1995; 103: 6104.
29. Vydrov OA, Scuseria GE, Assessment of a long-range corrected hybrid functional. J. Chem. Phys., 2006; 125: 234109.
30. Breneman CM, Wiberg KB, Determining atom-centered monopoles from molecular electrostatic potentials - the need for high sampling density in formamide conformational-analysis. J. Comp. Chem., 1990; 11: 361-373.
31. S. Simon MD, Dannenberg JJ, How does basis set superposition error change the potential surfaces for hydrogen bonded dimers? J. Chem. Phys., 1996; 105: 11024-11031.
