DFT/TDDFT study on the excited-state hydrogen bonding dynamics of hydrogen-bonded complex formed by methyl cyanide and methanol

Wang, Hongfei; Wang, Meishan; Liu, Enfu; Xin, Mingliang

doi:10.1016/j.comptc.2010.12.034

Cited by 24 publications

(10 citation statements)

References 76 publications

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“…Recently, similar calculations showing the hydrogen bonding effect on the electronic spectra have been made for methyl cyanide 24 and methyl isocyanide 25 in methanol. Many molecules of donor-acceptor character, often used as probes, can form hydrogen bonds with protic solvent molecules in their ground and excited electronic states.…”

Section: Introductionmentioning

confidence: 69%

Change in energy of hydrogen bonds upon excitation of 6-aminocoumarin: TDDFT/EFP1 study

Ramegowda¹

2013

New J. Chem.

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Density functional theory (DFT)/time dependent density functional theory (TDDFT) calculations combined with the effective fragment potential (EFP) method have been carried out to study the electronic structure and the excited state properties of 6-aminocoumarin (6AC) with five water molecules (6AC-(H 2 O) 5 complex). Ground-state geometries are optimized using DFT with the B3LYP functional combined with cc-pVDZ basis sets and transition energies are computed with the same basis set and functional. One intermolecular hydrogen bond (HB) NÁ Á ÁH-O (type A) is formed between the amino group of 6AC and one water molecule, two intermolecular HBs CQOÁ Á ÁH-O (type B) are formed between the carbonyl group of 6AC and two water molecules, and two HBs of N-HÁ Á ÁO (type C), via participation of their amino hydrogen atoms, with the oxygen atoms of water molecules. The change in hydrogen bond energy, DE HB of the 6AC-(H 2 O) 5 molecule and DE HB for each HB of the 6AC-(H 2 O) 5 molecule are calculatedseparately. Upon excitation of the 6AC-(H 2 O) 5 complex, the A type HB is weakened with a decrease of 11.03 kJ mol À1 energy, whereas B and C type HBs are strengthened with increases of 5.28 and 18.14 kJ mol À1 energy, respectively. In this theoretical work, DE HB is calculated using the procedure proposed by T. Nagata et al. to calculate solute-solvent interaction energy in J. Chem. Phys., 2011, 134, 034110 and this study also confirmed again that intermolecular hydrogen bonds between the 6AC chromophore and aqueous solvents are strengthened, not cleaved upon electronic excitation, which is in accordance with Zhao's works Wiley Periodicals, Inc. J. Comput. Chem., 2011.

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Section: Introductionmentioning

confidence: 69%

Change in energy of hydrogen bonds upon excitation of 6-aminocoumarin: TDDFT/EFP1 study

Ramegowda¹

2013

New J. Chem.

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“…On the other hand, excited-state hydrogen bond weakening can heighten the excitation energy of a related excited state and induce an electronic spectral blueshift. Recently similar calculations showing the hydrogen bonding effect on the electronic spectra have been made for methyl cyanide 16 and methyl isocyanide 17 in methanol.…”

Section: Introductionmentioning

confidence: 74%

Changes in energy of three types of hydrogen bonds upon excitation of aminocoumarins determined from absorption solvatochromic experiments

Krystkowiak

Maciejewski

2011

Phys. Chem. Chem. Phys.

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Absorption spectra of 6-aminocoumarin (6AC) and 7-aminocoumarins (C120 and C151) were studied in polyfluorinated alcohols: (1,1,1,3,3,3-hexafluoroisopropanol (HFIP), 2,2,2-trifluoroethanol (TFE)), in water and in methanol, and compared to those taken in 1-chloro-n-alkanes. According to our results, the observed unusual blue-shift of a long-wavelength band in absorption spectra in strong protic solvents is direct evidence of significant weakening of a NH-O hydrogen bond. The results obtained for the aminocoumarins in HFIP, which in contrast to aliphatic alcohols does not form hydrogen bonds of the acceptor type, prove that the decrease in the energy of the NH-O hydrogen bond upon excitation to the lowest S(1)-LE state is significantly greater than the increase in the energy of hydrogen bonds made by the oxygen atom of carbonyl group OH-O. It is in contrast to theoretical calculations for C151 [Y. Liu, J. Ding, R. Liu, D. Shi and J. Sun, J. Photochem. Photobiol. A, 2009, 201, 203-207]. A comparison of the absorption spectra measured in DMSO and in 1-chloro-n-alkanes shows that the energy of two N-HO hydrogen bonds considerably increases as a result of excitation. These results are consistent with those of the theoretical calculations [Y. Liu, J. Ding, R. Liu, D. Shi and J. Sun, J. Photochem. Photobiol. A, 2009, 201, 203-207; P. Zhou, P. Song, J. Liu, K. Han and G. He, Phys. Chem. Chem. Phys., 2009, 11, 9440-9449]. In this study we applied the procedure proposed by us in J. Photochem. Photobiol. A, 2006, 184, 250-264 for the determination of changes in hydrogen bond energy as a result of electronic excitation based on analysis of the absorption spectra of the probe studied in the solvents interacting with it exclusively nonspecifically and in those forming hydrogen bonds with it.

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“…Intermolecular non-covalent interactions (NCIs), such as hydrogen bonds, halogen bonds, pÁ Á Áp stacking and XÁ Á ÁH/p interactions, play an important role in molecular orientation, assembly, the stability in the crystal structure, the dynamic properties of biological molecules, and chemical reactions. 1,2 For the past several decades, scientists have been trying to explain NCIs and their roles in the above processes through well-defined quantum chemical concepts; however, the study of NCIs continues to be a challenging problem in science. Hydrogen bonding is a ubiquitous electrostatic NCI that is stabilized by electrostatic dipole interactions, dispersion and charge transfer between acceptor and donor atoms.…”

Section: Introductionmentioning

confidence: 99%

“…Three types of interactions are noticeable in the arrangement of a crystal structure: (1) the interaction between partially negative and partially positive charges or s-holes occurring due to polarizability (e.g. hydrogen and halogen bonds between Lewis acid-base pairs), (2) the interaction between a negative region (created by resonance), which is in the p-orbital due to resonance (e.g. CÁ Á ÁH/p and OÁ Á ÁH/p interactions) and partially positive charges or s-holes, (3) the interaction between a partially negative charge and the positive region (created by resonance), which is also in the p-orbital due to resonance (e.g.…”

Section: Introductionmentioning

confidence: 99%

On the nature of non-covalent interactions in isomers of 2,5-dichloro-1,4-benzoquinone dimers – ground- and excited-state properties

Pandiyan

Deepa

Kolandaivel

2014

Phys. Chem. Chem. Phys.

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The competition between non-covalent interactions (NCIs), such as C-H∙∙∙O, C-H∙∙∙Cl, C-Cl∙∙∙O, C-Cl∙∙∙Cl-C, C-O∙∙∙C, C-Cl∙∙∙C and C-O∙∙∙π, in the isomers of the 2,5-dichloro-1,4-benzoquinone (DCBQ) dimer were investigated by quantum chemical calculations to study the properties of the ground and excited states. All the interactions were identified through bond critical points (BCP) with an atoms in molecule (AIM) study. Isomer 1 (IH) and isomer 6 (IP) were surprisingly very stable, and the largest stabilization energies of 4.16 and 5.39 kcal mol(-1), respectively, were observed for the ground state and 5.67 and 6.07 kcal mol(-1), respectively, were observed for the excited state at the MP2/6-31++G(d,p) level of theory. The orientations of the excited-state isomers were similar to those of the ground-state except for isomer 5 (IX) and isomer 9 (IM), which disturbed the relative energy stability order. The calculated absorption spectra have shown two absorption splits for isomers 5, 7, 8 and 9 through the acute angle between the transition dipole moment of the monomers. The circular dichroism (CD) couplet of the CD spectrum and the value of optical rotation (OR) have indicated that isomers 1, 3, 5, 7, 8 and 9 have chiral characteristics. The study of the absorption and CD spectra has revealed the impact of intermolecular NCIs on chirality.

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DFT/TDDFT study on the excited-state hydrogen bonding dynamics of hydrogen-bonded complex formed by methyl cyanide and methanol

Cited by 24 publications

References 76 publications

Change in energy of hydrogen bonds upon excitation of 6-aminocoumarin: TDDFT/EFP1 study

Change in energy of hydrogen bonds upon excitation of 6-aminocoumarin: TDDFT/EFP1 study

Changes in energy of three types of hydrogen bonds upon excitation of aminocoumarins determined from absorption solvatochromic experiments

On the nature of non-covalent interactions in isomers of 2,5-dichloro-1,4-benzoquinone dimers – ground- and excited-state properties

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