Characteristics and nature of the intermolecular interactions in boron-bonded complexes with carbene as electron donor: An ab initio, SAPT and QTAIM study

Journal of Molecular Modeling

Volumn 18, Issue 5, 2012, Pages 2003-2011

  Esrafili, Mehdi D ^a  

^a UNIVERSITY OF MARAGHEH   (Iran)

Author keywords

Ab initio; Carbene; QTAIM; Symmetry adapted perturbation theory

Indexed keywords

BORON DERIVATIVE; CARBENE;

AB INITIO CALCULATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; COMPLEX FORMATION; COVALENT BOND; ENERGY; MOLECULAR INTERACTION; PRIORITY JOURNAL; QUANTUM THEORY; SYMMETRY ADAPTED PERTURBATION THEORY; THEORY;

BORON; BORON COMPOUNDS; ELECTRONS; HYDROGEN BONDING; KINETICS; METHANE; MODELS, CHEMICAL; QUANTUM THEORY; STATIC ELECTRICITY; THERMODYNAMICS;

EID: 84861228571     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-011-1221-2     Document Type: Article

References (55)

1. Woo HK, Wang XB, Wang LS, Lu KC (2005) Probing the lowbarrier hydrogen bond in hydrogen maleate in the gas phase: a. photoelectron spectroscopy and ab initio study. J Phys Chem A 109:10633-10637
2. Hobza P, Havlas Z (2000) Blue-shifting hydrogen bonds. Chem Rev 100:4253-4264 (Pubitemid 32067767)
3. Scheiner S (1997) Hydrogen bonding: a theoretical prospective. Oxford University Press, Oxford, U.K.
4. Thar J, Kirchner B (2006) Hydrogen bond detection. J Phys Chem A 110:4229-4237
5. Hong BH, Lee JY, Lee CW, Kim JC, Bae SC, Kim KS (2001) Selfassembled arrays of organic nanotubes with infinitely long onedimensional H-bond chains. J Am Chem Soc 123:10748-10749 (Pubitemid 33015724)
6. Hong BH, Bae SC, Lee CW, Jeong S, Kim KS (2001) Ultrathin single-crystalline silver nanowire arrays formed in an ambient solution phase. Science 294:348-351 (Pubitemid 32963397)
7. Tarakeshwar P, Kim KS (2004) In: Encyclopedia of nanoscience and nanotechnology, vol 7. American Science Publishers, California, pp 367-404
8. Bandyopadhyay I, Lee HM, Kim KS (2005) Phenol vs water molecule interacting with various molecules: σ-type, π-type, and ?-type hydrogen bonds, interaction energies, and their energy components. J Phys Chem A 109:1720-1728 (Pubitemid 40356130)
9. Regitz M (1996) Nucleophilic carbenes: an incredible renaissance. Angew Chem 35:725-728
10. Bourissou D, Guerret O, Gabbaï FP, Bertrand G (2000) Stable carbenes. Chem Rev 100:39-91
11. Couzijn EPA, Zocher E, Bach A, Chen P (2010) Gas-phase energetics of reductive elimination from a palladium (II) Nheterocyclic carbene complex. Chem Eur J 16:5408-5415
12. Benitez D, Shapiro ND, Tkatchouk E, Wang Y, Goddard WA III, Toste FD (2009) A bonding model for gold(I) carbene complexes. Nature Chem 1:482-486
13. Yao S, Xiong Y, Driess M (2010) N-heterocyclic carbene (NHC)- stabilized silanechalcogenones: NHC→Si(R2)=E (E=O, S, Se, Te). Chem Eur J 16:1281-1288
14. Liu Z (2009) Chemical bonding in silicon-carbene complexes. J Phys Chem A 113:6410-6414
15. Standard JM, Steidl RJ, Beecher MC, Quandt RW (2011) Multireference configuration interaction study of bromocarbenes. J Phys Chem A 115:1243-1249
16. Alkorta I, Rozas I, Elguero J (1998) Non-conventional hydrogen bonds. Chem Soc Rev 27:163-170
17. Nolan SP (2006) N-Heterocyclic carbenes in synthesis. Wiley, New York
18. Enders D, Breuer K, Raabe G, Runsink J, Teles JH, Melder JP, Ebel K, Brode S (1995) Preparation, structure, and reactivity of 1,3,4-Triphenyl-4,5- dihydro-1H-1,2,4-triazol-5-ylidene, a new stable carbene. Angew Chem Int Edn Eng 34:1021-1023
19. Grasa GA, Kissling RM, Nolan SP (2002) N-Heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions. Org Lett 4:3583-3586
20. Glorius F (2006) N-Heterocyclic carbenes in transition metal catalysis (Topics in Organometallic Chemistry). Springer, Heidelberg
21. Ullah F, Kindermann MK, Jones PG, Heinicke J (2009) Annulated N-Heterocyclic carbenes: 1,3-ditolylphenanthreno [9,10-d]imidazol- 2-ylidene and transition metal complexes thereof. Organometallics 28:2441-2449
22. Khramov DM, Lynch VM, Bielawski CW (2007) N-Heterocyclic carbene-transition metal complexes: spectroscopic and crystallographic analyses of π-back-bonding interactions. Organometallics 26:6042-6049 (Pubitemid 350208126)
23. Moya-Barrios R, Fregeau BM, Cozens FL (2009) Reactivity of halo(pyridinium) carbenes. J Org Chem 74:9126-9131
24. Padwa A, Hornbuckle SF (1991) Ylide formation from the reaction of carbenes and carbenoids with heteroatom lone pairs. Chem Rev 91:263-309
25. Wanzlick HW, Schönherr HJ (1970) Liebigs Ann Chem 731:176
26. Li Q, Wang H, Liu Z, Li W, Cheng J, Gong B, Sun J (2009) Ab initio study of lithium-bonded complexes with carbene as an electron donor. J Phys Chem A 113:14156-14160
27. Kitaura K, Morokuma K (1976) A new energy decomposition scheme for molecular interactions within the Hartree-Fock approximation. Int J Quantum Chem 10:325-340
28. Jeziorski B, Moszynski R, Szalewicz K (1994) Perturbation theory approach to intermolecular potential energy surfaces of van der Waals Complexes. Chem Rev 94:1887-1930 (Pubitemid 124000190)
29. Williams HL, Szalewicz K, Jeziorski B, Moszynski R, Rybak S (1993) Symmetry-adapted perturbation theory calculation of the Ar-H2 intermolecular potential energy surface. J Chem Phys 98:1279-1292
30. Misquitta AJ, Podeszwa R, Jeziorski B, Szalewicz K (2005) Intermolecular potentials based on symmetry-adapted perturbation theory with dispersion energies from time-dependent densityfunctional calculations. J Chem Phys 123:214103-214116
31. Misquitta AJ, Szalewicz K (2005) Symmetry-adapted perturbation-theory calculations of intermolecular forces employing density-functional description of monomers. J Chem Phys 122:214109-214127
32. Williams HL, Chabalowski CF (2001) Using Kohn-Sham orbitals in symmetry-adapted perturbation theory to investigate intermolecular interactions. J Phys Chem A 105:646-659
33. Bader RFW (1990) Atoms in molecules-a quantum theory. Oxford University Press, New York
34. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA (1993) General atomic and molecular electronic structure system. J Comput Chem 14:1347-1363
35. Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098-3100
36. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785-789
37. Hobza R, Zahradnik R (1988) Intermolecular Interactions between Medium-Sized Systems. Nonempirical and empirical calculations of interaction energies: successes and failures. Chem Rev 88:871-897
38. Boys SF, Bernardi F (1970) The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol Phys 19:553-566
39. Hesselmann A, Jansen G (2003) The helium dimer potential from a combined density functional theory and symmetry-adapted perturbation theory approach using an exact exchange-correlation. Phys Chem Chem Phys 5:5010-5014
40. Hesselmann A, Jansen G (2003) Intermolecular dispersion energies from time-dependent density functional theory. Chem Phys Lett 367:778-784
41. Jansen G, Hesselmann A (2001) Comment on: using Kohn-Sham orbitals in symmetry-adapted perturbation theory to investigate intermolecular interactions. J Phys Chem A 105:11156-11157
42. Dalton, a molecular electronic structure program, Release 2.0 (2005) see http://www.kjemi.uio.no/software/dalton/dalton.html
43. Bukowski R, Cencek W et al. (2008) SAPT 2008: an Ab Initio program for many-body symmetry-adapted perturbation theory calculations of intermolecular interaction energies. Sequential and Parallel Versions, University of Delaware and University of Warsaw, 2008; see http://www.physics.udel.edu/-szalewic/SAPT/ SAPT.html
44. Biegler-Konig F, Schonbohm J, Bayles D (2001) AIM 2000. J Comput Chem 22:545-559
45. Liu Z (2010) On the nature of B-Ccarbene bonding in a stable neutral diborene. J Chem Phys 132:084303-084309
46. Alkorta I, Elguero J (1996) carbenes and silylenes as hydrogen bond acceptors. J Phys Chem 100:19367-19370 (Pubitemid 126786972)
47. Jaffe RL, Smith GD (1996) A quantum chemistry study of benzene dimer. J Chem Phys 105:2780-2788 (Pubitemid 126573015)
48. Esrafili MD, Beheshtian J, Hadipour NL (2011) Computational study on the characteristics of the interaction in linear urea clusters. Int J Quantum Chem 111:3184-3195
49. Cybulski H, Sadlej J (2008) Symmetry-adapted perturbationtheory interaction-energy decomposition for hydrogen-bonded and stacking structures. J Chem Theor Comput 4:892-897
50. Panek JJ, Jezierska A (2007) Symmetry-adapted perturbation theory analysis of the N···HX hydrogen Bonds. J Phys Chem 111:650-655
51. Koch U, Popelier PLA (1995) Characterization of C- H···O hydrogen bonds on the basis of the charge density. J Phys Chem 99:9747-9754
52. Rozas I, Alkorta I, Elguero (2000) Behaviour of ylides containing N, O and C atoms as hydrogen bond acceptors. J Am Chem Soc 122:11154-11161
53. Lu Y, Zou J, Wang Y, Jiang Y, Yu Q (2007) Ab initio investigation of the complexes between bromobenzene and several electron donors: some insights into the magnitude and nature of halogen bonding. J Phys Chem A 111:10781-10788 (Pubitemid 350046149)
54. Espinosa E, Molins E, Lecomte C (1998) Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chem Phys Lett 285:170-173 (Pubitemid 128180262)
55. Abramov YA (1997) On the possibility of kinetic energy density evaluation from the experimental electron-density distribution. Acta Crystallogr Sect A Found Crystallogr 53:264-272