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Volumn 13, Issue 2, 2009, Pages 149-171

Theoretical insights into material properties of Schiff bases and related azo compounds

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETICS; COMPUTATIONAL CHEMISTRY; DESIGN FOR TESTABILITY; MATERIALS PROPERTIES;

EID: 65249149154     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527209787193747     Document Type: Review
Times cited : (27)

References (299)
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    • As stressed by Cramer, 2] statements like 'the PROG1 optimized structure, where PROG1 stands for a particular software package, are completely unacceptable. Results obtained with a particular method should be completely independent of the code used. If PROG1 and PROG2 do not give identical numbers, then one or both of them contain a bug. However, be sure to use really the same method: for instance, some software packages use in MP2 calculations by default a frozen core, whereas others, also by default, do not freeze any orbitals. Obviously, MP2 results obtained by these two packages, even if the same convergence criteria have been used, will be different. Particularly problematic in this respect are the now very popular density functional theory methods where integration is commonly carried out numerically on a grid. To be comparable, results must have been obtained with exactly the same grid. The default grids used by different programs can vary quite substantially! Since furthermor
    • As stressed by Cramer, [2] statements like 'the PROG1 optimized structure', where PROG1 stands for a particular software package, are completely unacceptable. Results obtained with a particular method should be completely independent of the code used. If PROG1 and PROG2 do not give identical numbers, then one or both of them contain a bug. However, be sure to use really the same method: for instance, some software packages use in MP2 calculations by default a frozen core, whereas others, also by default, do not freeze any orbitals. Obviously, MP2 results obtained by these two packages, even if the same convergence criteria have been used, will be different. Particularly problematic in this respect are the now very popular density functional theory methods where integration is commonly carried out numerically on a grid. To be comparable, results must have been obtained with exactly the same grid. The default grids used by different programs can vary quite substantially! Since furthermore the exact meaning of a certain keyword might vary between different versions of one and the same software package, a proper "Computational details" section should apart from quoting the model used, including the necessary technical details (convergence criteria, grid,.)
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    • also cite the software and version number.
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    • Unfortunately many of these modifications have been done within certain software packages without publication in scientific journals. This has led to the very unsatisfactory situation that the meaning of AM1 or PM3 and thus, results obtained thereby, may depend on the software used. The promise to make all parametrisation freely available and to publish all modifications to methods [17] is greatly appreciated
    • Unfortunately many of these modifications have been done within certain software packages without publication in scientific journals. This has led to the very unsatisfactory situation that the meaning of AM1 or PM3 and thus, results obtained thereby, may depend on the software used. The promise to make all parametrisation freely available and to publish all modifications to methods [17] is greatly appreciated.
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    • An isodesmic reaction is one in which the total number of each type of bond is identical on both sides of the reaction
    • An isodesmic reaction is one in which the total number of each type of bond is identical on both sides of the reaction.
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    • Size-consistency means that the energy for a N-particle system at infinite separation equals the sum of the energies calculated for each one of the N particles separately.
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    • Even for moderately sized molecules, be prepared for several months of computer time when using this method
    • Even for moderately sized molecules, be prepared for several months of computer time when using this method.
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    • Most of these functionals are accessed in electronic structure software by letter and possibly year codes. Which acronym actually stands for a certain functional might depend on the respective software. So some care is necessary in comparing DFT calculations done with different programs apart from grid issues
    • Most of these functionals are accessed in electronic structure software by letter and possibly year codes. Which acronym actually stands for a certain functional might depend on the respective software. So some care is necessary in comparing DFT calculations done with different programs (apart from grid issues).
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    • (b) See also Morokuma et al. [133]
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    • -1 result. [45a]
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    • For instance, a double-ζ basis set should have d functions on heavy atoms and p functions on hydrogen; a triple-ζ basis should include two sets of d and one of f functions on heavy atoms and two sets of p and one of d functions on H
    • For instance, a double-ζ basis set should have d functions on heavy atoms and p functions on hydrogen; a triple-ζ basis should include two sets of d and one of f functions on heavy atoms and two sets of p and one of d functions on H.
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    • Especially for elements of the 3d block the popular LANL2DZ basis might not be appropriate, see ref. [44] Henson, Hay and Redondo also have pointed out that for a correct description of oxygen binding by Schiff base - cobalt complexes a basis set more flexible than LANL2DZ is necessary: Henson, N.J.; Hay, P.J.; Redondo, A. Inorg. Chem., 1999, 38, 1618.
    • Especially for elements of the 3d block the popular LANL2DZ basis might not be appropriate, see ref. [44] Henson, Hay and Redondo also have pointed out that for a correct description of oxygen binding by Schiff base - cobalt complexes a basis set more flexible than LANL2DZ is necessary: Henson, N.J.; Hay, P.J.; Redondo, A. Inorg. Chem., 1999, 38, 1618.
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    • Other technical issues relate to the handling of d functions (spherical vs Cartesian) or the type of contraction (segmented vs general contractions, this depends on the software used and should be checked beforehand. It is also a good idea to print out the basis set to check whether one really uses the intended basis set. For instance, instance, in several papers describing ab initio calculation of first hyperpolarisabilities of Schiff base ligands and their metal complexes, the 3-21+G** basis set was used. However, in the standard definition of the 3-21G* basis set [more appropriately denoted as 3-21G*, d-type polarization functions are only added to second-row elements. Thus, with 3-21+G** there would be p-type polarisation functions on hydrogen but no polarisation functions at all on carbon, nitrogen, and oxygen
    • Other technical issues relate to the handling of d functions (spherical vs Cartesian) or the type of contraction (segmented vs general contractions); this depends on the software used and should be checked beforehand. It is also a good idea to print out the basis set to check whether one really uses the intended basis set. For instance, instance, in several papers describing ab initio calculation of first hyperpolarisabilities of Schiff base ligands and their metal complexes, the 3-21+G** basis set was used. However, in the "standard" definition of the 3-21G* basis set [more appropriately denoted as 3-21G(*)], d-type polarization functions are only added to second-row elements. Thus, with 3-21+G** there would be p-type polarisation functions on hydrogen but no polarisation functions at all on carbon, nitrogen, and oxygen.
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    • All popular quantum chemistry program packages offer at least one continuum solvation model. In most cases the user can choose between several variants. These variants mainly differ in the construction of the cavity, number of grid points, tessellation as well as whether and how non-electrostatic terms (dispersion, cavitation) are taken into account
    • All popular quantum chemistry program packages offer at least one continuum solvation model. In most cases the user can choose between several variants. These variants mainly differ in the construction of the cavity, number of grid points, tessellation as well as whether and how non-electrostatic terms (dispersion, cavitation) are taken into account.
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    • for formation of 2-arylbenzimidiazoles resulting from cyclisation/ oxidation of mono-Schiffbases of diamines, see ref. [117]
    • (c) for formation of 2-arylbenzimidiazoles resulting from cyclisation/ oxidation of mono-Schiffbases of diamines, see ref. [117]
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    • See, for instance, the references cited in ref, 85
    • See, for instance, the references cited in ref. [85]
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    • A caveat: the default grids implemented in the various software packages can be quite different
    • A caveat: the default grids implemented in the various software packages can be quite different.
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    • (e) T.; Okada, Y.; Morita, Z. Dyes Pigm., 2007, 73, 141.
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    • For a review of quantum chemical methods for the calculation of photophysical and photochemical processes, see: Serrano-Andres, L. Merchan, M. J. Mol. Struct, Theochem, 2005, 729, 99
    • (b) For a review of quantum chemical methods for the calculation of photophysical and photochemical processes, see: Serrano-Andres, L. Merchan, M. J. Mol. Struct. (Theochem), 2005, 729, 99.
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    • High-level calculations on the photophysics of salicylic acid: Sobolewski, A.L.; Domcke, W. Phys. Chem. Chem. Phys., 2006, 8, 3410.
    • (c) High-level calculations on the photophysics of salicylic acid: Sobolewski, A.L.; Domcke, W. Phys. Chem. Chem. Phys., 2006, 8, 3410.
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    • The quantity μβ is given by μβ, μ xβx, μyβ y, μzβz, where the μ i are the components of the dipole moment μ and the βi are defined by βi=β iii+1/3∑j≠j(β ijj+βjij+βjji) Sometimes this quantity is multiplied by a factor 3/5 or the factor 1/5 is included in the definition of the βi. Instead of the power series expansion, equ (8, sometimes a Taylor series is used, with the factors 1/(2, 1/(3, either part of the definition of the individual hyperpolarisabilities or not. Adding to the confusion is that the quantities βvec=μβ/ υ and β tol=(βx2+βy 2+βz2)1/2 sometimes are denoted as β
    • -1, for unit conversion, see Shelton and Rice [103]. For other problems when comparing experimental and calculated hyperpolarisabilities, see: A. Willetts, J.E. Rice, D.M. Burland and D.P. Shelton, J. Chem. Phys., 97, 7590 (1992)]. Finally, μβ-values also depend on the frequency of the exciting laser and solvent. Thus, when comparing EFISH results from different sources considerable care has to be exercised.
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    • (c) Van Gisbergen, S.J.A.; Snijders, J. G.; Baerends, E.J. J. Chem. Phys., 1998, 109, 10644; correction to Table III in this paper: J. Chem. Phys., 1999, 111, 6652.
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    • Ferrighi, L, Frediani, L, Cappelli, Ch, Sałek, P, Ågren, H, Helgaker, T, Ruud, K. Chem. Phys. Lett, 2006, 425, 267. The pushpull phenylpolyenes treated in this paper nicely illustrate the problems of density functionals to describe long-range electron transfer correctly. B3LYP and CAM-B3LYP (designed in an attempt to correct for the shortcomings of B3LYP) hyperpolarisabilities are similar for the first member in the series and diverge with increasing length of the polyene chain. It also shows that these Coulomb-attenuated-methods are still in a development phase. Recently, a density functional for spectroscopy without long-range self-interaction error has been described: Y. Zhao and D.G. Truhlar, J. Phys. Chem. A, ASAP paper published on the Web 17-Nov-2006
    • Ferrighi, L.; Frediani, L.; Cappelli, Ch.; Sałek, P.; Ågren, H.; Helgaker, T.; Ruud, K. Chem. Phys. Lett., 2006, 425, 267. The pushpull phenylpolyenes treated in this paper nicely illustrate the problems of density functionals to describe long-range electron transfer correctly. B3LYP and CAM-B3LYP (designed in an attempt to correct for the shortcomings of B3LYP) hyperpolarisabilities are similar for the first member in the series and diverge with increasing length of the polyene chain. It also shows that these Coulomb-attenuated-methods are still in a development phase. Recently, a "density functional for spectroscopy" without long-range self-interaction error has been described: Y. Zhao and D.G. Truhlar, J. Phys. Chem. A, ASAP paper published on the Web 17-Nov-2006.
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    • There is ongoing development in this field with respect to efficient implementation into ab initio and/or DFT codes. Different software packages offer different approaches or, more precisely, intend to offer them in future releases
    • There is ongoing development in this field with respect to efficient implementation into ab initio and/or DFT codes. Different software packages offer different approaches or, more precisely, intend to offer them in future releases!
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    • Second Harmonic Generation with Schiff Bases,
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    • Palazzotto, M.C. Second Harmonic Generation with Schiff Bases, US Patent, 4733109, March 22, 1988.
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    • For a short summary of mechanistic aspects including computational results, see: Limberg, C. Angew. Chem. Int. Ed., 2003, 42, 5932.
    • For a short summary of mechanistic aspects including computational results, see: Limberg, C. Angew. Chem. Int. Ed., 2003, 42, 5932.
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    • V=O species. Experimental evidence and calculated activation energies suggest that the singlet state can be neglected in the catalytic cycle, see ref. [148] and references cited therein.
    • V=O species. Experimental evidence and calculated activation energies suggest that the singlet state can be neglected in the catalytic cycle, see ref. [148] and references cited therein.
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    • To rationalise the observed diastereoselectivity in vinylcyclopropane epoxidations, multiple oxygenating species as well as a bifurcation in the catalytic cycle between a stepwise radical and a concerted, Lewis acid activated, step has been proposed: Adam, W.; Roschmann, K.J.; Saha-Möller, C.R.; Seebach, D. J. Am. Chem. Soc., 2002, 124, 5068.
    • (a) To rationalise the observed diastereoselectivity in vinylcyclopropane epoxidations, multiple oxygenating species as well as a bifurcation in the catalytic cycle between a stepwise radical and a concerted, Lewis acid activated, step has been proposed: Adam, W.; Roschmann, K.J.; Saha-Möller, C.R.; Seebach, D. J. Am. Chem. Soc., 2002, 124, 5068.
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    • For the effect of the donor ligand on the nature of the oxygenating species, see
    • (b) For the effect of the donor ligand on the nature of the oxygenating species, see: Collman, J.P.; Zheng, L.; Braumann, J.I. Inorg. Chem., 2004, 43, 2672.
    • (2004) Inorg. Chem , vol.43 , pp. 2672
    • Collman, J.P.1    Zheng, L.2    Braumann, J.I.3
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    • For a review of radical intermediates in metal-catalysed oxgenations, see ref, 132
    • For a review of radical intermediates in metal-catalysed oxgenations, see ref. [132]
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    • For a review on substituent electronic effects in chiral ligands, see
    • (a) For a review on substituent electronic effects in chiral ligands, see: Flanagan, S.P.; Guiry, P.G. J. Organomet. Chem., 2006, 691, 2125.
    • (2006) J. Organomet. Chem , vol.691 , pp. 2125
    • Flanagan, S.P.1    Guiry, P.G.2
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    • In cases where no simple correlation between enantioselectivity and substituent electronic character could be found multiple oxygenating species have been suggested: McGarrigle, E.M, Murphy, D.M, Gilheany, D.G. Tetrahedron Asymmetry, 2004, 15, 1343
    • (b) In cases where no simple correlation between enantioselectivity and substituent electronic character could be found multiple oxygenating species have been suggested: McGarrigle, E.M.; Murphy, D.M.; Gilheany, D.G. Tetrahedron Asymmetry, 2004, 15, 1343.
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    • Whether spin-crossing occurs or not will require location of minima of the seam of crossing (minimum energy crossing point, MSX, MECP). Code for this purpose is generally not yet part of most software packages but has become available recently [48a]. Besides, the amount of spin-orbit coupling is important for twostate reactivity to be observable. It should also be stressed that a proper choice of the basis set is crucial.
    • Whether spin-crossing occurs or not will require location of minima of the seam of crossing (minimum energy crossing point, MSX, MECP). Code for this purpose is generally not yet part of most software packages but has become available recently [48a]. Besides, the amount of spin-orbit coupling is important for twostate reactivity to be observable. It should also be stressed that a proper choice of the basis set is crucial.
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    • The change in notation from (R,R) to (S,S) in going from 21 to 22 is simply a result of the Cahn-Ingold-Prelog priority rules.
    • The change in notation from (R,R) to (S,S) in going from 21 to 22 is simply a result of the Cahn-Ingold-Prelog priority rules.
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    • For a criticism concerning the use of the BP86 functional in transition metal catalysed reactions as well as for O-O bond breaking processes, see ref. [133]
    • For a criticism concerning the use of the BP86 functional in transition metal catalysed reactions as well as for O-O bond breaking processes, see ref. [133]
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    • For a review of stereoselective cyclopropanation reactions, see
    • For a review of stereoselective cyclopropanation reactions, see: Lebel, H.; Marcoux, J-F.; Molinaro, C.; Charette, A.B. Chem. Rev., 2003, 103, 977.
    • (2003) Chem. Rev , vol.103 , pp. 977
    • Lebel, H.1    Marcoux, J.-F.2    Molinaro, C.3    Charette, A.B.4
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    • For calculations on transition metal-catalysed cyclopropanations with ligands other than Schiff bases, see: (a) Fraile, J.M, Garcia, J.I, Martinez-Merino, V, Mayoral, J.A, Salvatella, L. J. Am. Chem. Soc, 2001, 123, 7616
    • For calculations on transition metal-catalysed cyclopropanations with ligands other than Schiff bases, see: (a) Fraile, J.M.; Garcia, J.I.; Martinez-Merino, V.; Mayoral, J.A.; Salvatella, L. J. Am. Chem. Soc., 2001, 123, 7616.
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    • For an alternative model for asymmetric cyanohydrin formation catalysed by titanium-salen complexes based on X-ray crystallography, see: Ilyashenko, G, Motevalli, M, Watkinson, M. Tetrahedron Asymmetry, 2006, 17, 1625
    • (c) For an alternative model for asymmetric cyanohydrin formation catalysed by titanium-salen complexes based on X-ray crystallography, see: Ilyashenko, G.; Motevalli, M.; Watkinson, M. Tetrahedron Asymmetry, 2006, 17, 1625.
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    • This is in contrast to a bis(radical) derived from triphenylphosphane substituted by nitronyl nitroxide moieties. Here the bridging H2O was found to induce ferromagnetic coupling: Rancurel, C, Daro, N, Borobia, O.B, Herdtweck, E, Sutter, J.-P. Eur. J. Org. Chem, 2003, 167
    • This is in contrast to a bis(radical) derived from triphenylphosphane substituted by nitronyl nitroxide moieties. Here the bridging H2O was found to induce ferromagnetic coupling: Rancurel, C.; Daro, N.; Borobia, O.B.; Herdtweck, E.; Sutter, J.-P. Eur. J. Org. Chem., 2003, 167.
  • 278
    • 85200277895 scopus 로고    scopus 로고
    • Exchange coupling constants in homo- and heterobinuclear transition metal complexes can be calculated by the broken-symmetry approach: Ruiz, E, Cano, J, Alvarez, S, Alemany, P. J. Comput. Chem, 1999, 20, 1391. This paper also contains a comparison of the accuracy of different hybrid density functionals
    • Exchange coupling constants in homo- and heterobinuclear transition metal complexes can be calculated by the broken-symmetry approach: Ruiz, E.; Cano, J.; Alvarez, S.; Alemany, P. J. Comput. Chem., 1999, 20, 1391. This paper also contains a comparison of the accuracy of different hybrid density functionals.
  • 279
    • 85200278006 scopus 로고    scopus 로고
    • For a theoretical treatment of exchange coupling via hydrogen bonding in binuclear copper complexes, see: Desplanches, C, Ruiz, E, Rodriguez-Fortea, A, Alvarez, S. J. Am. Chem. Soc, 2002, 124, 5197
    • For a theoretical treatment of exchange coupling via hydrogen bonding in binuclear copper complexes, see: Desplanches, C.; Ruiz, E.; Rodriguez-Fortea, A.; Alvarez, S. J. Am. Chem. Soc., 2002, 124, 5197.
  • 294
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    • Chatziefthimiou, S.D.; Lazarou, Y.G.; Hadjoudis, E.; Dziembowska, T.; Mavridis, I.M. J. Phys. Chem. B, ASAP article published on the Web 11/07/2006.
    • Chatziefthimiou, S.D.; Lazarou, Y.G.; Hadjoudis, E.; Dziembowska, T.; Mavridis, I.M. J. Phys. Chem. B, ASAP article published on the Web 11/07/2006.
  • 295
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    • Dispersion can make an important contribution to intermolecular interaction energies; since this is not accounted for by DFT, costly (possibly prohibitive) MP2 calculations might be necessary. A possible solution to this dilemma might be the newly developed dispersion- corrected DFT DFT-D, Antony, J, Grimme, S. Phys. Chem. Chem. Phys, 2006, 8, 5287
    • Dispersion can make an important contribution to intermolecular interaction energies; since this is not accounted for by DFT, costly (possibly prohibitive) MP2 calculations might be necessary. A possible
  • 296
    • 85200277497 scopus 로고    scopus 로고
    • Zhao, L.; Sui, D.; Chai, J.; Wang, Y.; Jiang, S. J. Phys. Chem. B, ASAP article published on the Web 11/09/2006. possibility of an electric field induced NLO switch by rotation of the two boronate groups A: Lamere, J. F.; Lacroix, P.G.; Farfan, N.; Rivera, J.M.; Santillan, R.; Nakatani, K. J. Mat. Chem., 2006, 16, 2913.
    • Zhao, L.; Sui, D.; Chai, J.; Wang, Y.; Jiang, S. J. Phys. Chem. B, ASAP article published on the Web 11/09/2006. possibility of an electric field induced NLO switch by rotation of the two boronate groups A: Lamere, J. F.; Lacroix, P.G.; Farfan, N.; Rivera, J.M.; Santillan, R.; Nakatani, K. J. Mat. Chem., 2006, 16, 2913.
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    • 85200278007 scopus 로고    scopus 로고
    • The importance of ortho-fluorine substituents on the N-aryl group in bis(phenoxy-imin)Ti catalysts (B) on the living propylene polymerisation has been investigated by DFT and QM/MM methods: Talarico, G.; Cavallo, L. Kinet. Catal., 2006, 47, 289. The key factor was found to be the steric repulsion of the fluorine-substituted rings with the growing polymer chain and an incoming propene molecule.
    • The importance of ortho-fluorine substituents on the N-aryl group in bis(phenoxy-imin)Ti catalysts (B) on the living propylene polymerisation has been investigated by DFT and QM/MM methods: Talarico, G.; Cavallo, L. Kinet. Catal., 2006, 47, 289. The key factor was found to be the steric repulsion of the fluorine-substituted rings with the growing polymer chain and an incoming propene molecule.
  • 298
    • 85200276405 scopus 로고    scopus 로고
    • In close relation to Schiff base complexes as catalysts for oxygenation reactions and/or catalase mimics, density functional calculations have been used to suggest design strategies for biomimetic models of dopamine α-monooxygenase and peptidylglycine α-hydroxylating monooxygenase, e.g. the anilino-imine copper complexes C: Gherman, B.F, Tolman, W.B, Cramer, C.J. J. Comput. Chem, 2006, 27, 1950
    • In close relation to Schiff base complexes as catalysts for oxygenation reactions and/or catalase mimics, density functional calculations have been used to suggest design strategies for biomimetic models of dopamine α-monooxygenase and peptidylglycine α-hydroxylating monooxygenase, e.g. the anilino-imine copper complexes C: Gherman, B.F.; Tolman, W.B.; Cramer, C.J. J. Comput. Chem., 2006, 27, 1950.
  • 299
    • 85200277323 scopus 로고    scopus 로고
    • III) sal(oph)en complexes D: Lo, W.-K.; Wong, W.-K.; Wong, W.-Y.; Guo, J.; Yeung, K.-T.; Cheng, Y.-K.; Yang, X.; Jones, R.A. Inorg. Chem., 2006, 45, 9315.
    • III) sal(oph)en complexes D: Lo, W.-K.; Wong, W.-K.; Wong, W.-Y.; Guo, J.; Yeung, K.-T.; Cheng, Y.-K.; Yang, X.; Jones, R.A. Inorg. Chem., 2006, 45, 9315.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.