Exploring the potential energy surfaces of association of NO with aminoacids and related organic functional groups: the role of entropy of association

Crespo‐Otero, Rachel; Pérez-Badell, Yoana; Padrón-García, Juan Alexander; Montero‐Cabrera, Luis A.

doi:10.1007/s00214-007-0346-y

Cited by 11 publications

(12 citation statements)

References 25 publications

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“…The larger stabilization of N orientated complexes with respect to the O orientated has also been obtained for other NO · · · small molecule complexes, like CH 4 · · · NO, H 2 O · · · NO, NH 3 · · · NO, etc. 15 The largest stabilization energies of N orientated complexes are in agreement with the largest electron densities obtained in the intermolecular bcp's.…”

Section: Resultssupporting

confidence: 77%

“…13,14 In a previous work, we analyzed the interaction between the amino acids and nitric oxide molecules at semiempirical level. 15 For polar amino acids, the interactions with lateral chains are energetically as stable as or even more stable than the interactions with the backbone atoms. Histidine (His) is a polar amino acid, which can change its charge in the physiological interval of pH.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Study of Imidazole···NO Complexes

et al. 2009

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A set of weak complexes between imidazole (Imi) and nitric oxide (NO) were calculated with UMP2/6-31++G(d,p) and UMP2/6-311++G(2d,2p) levels of theory. Planar and nonplanar geometries were considered. Complexes of NO and protonated imidazole (ImiH(+)) were also studied due to the biological important effect of Imi protonation. It was found that ring protonation increases the stability of planar complexes and does not affect significantly nonplanar complexes. The Z-H...XY (Z = C, N and X, Y = N, O) interactions resulted as hydrogen bonds according to Koch and Popelier criteria based on AIM theory. Charge transfer was also found very important for complex stabilization within our theoretical framework. Planar NO...ImiH(+) complexes are more stable than those obtained with neutral Imi.

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Section: Resultssupporting

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Theoretical Study of Imidazole···NO Complexes

et al. 2009

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“…Multiple Minima Hypersurface (MMH) methodology, which validity for the study of molecular associations and for conformational analysis has been widely demonstrated by some of the co-authors, [30][31][32][33][34][35][36][37][38] was employed for random generation and optimization at semiempirical level of theory of α−α'Py n SiOH (n = 2,3). Most stable structures were DFT-refined for conformational analysis.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolyl–Silicon Compounds as Precursors for Donor–Acceptor Systems Stabilized by Noncovalent Interactions

et al. 2015

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Pyrrolil-silicon compounds were investigated by different theoretical approaches.Model monomers consisted in pyrrole ring N-substituted with silylmethoxy and silylhydroxy end-groups through propyl chain spacer, designated as PySi and PySiOH. Geometrical, vibrational and electronic properties, as well as chemical reactivity, are discussed and compared with Pyrrole (Py) and N-propylpyrrole (N-PrPy) that were studied in parallel for reference purposes and methods validation. The electronic distribution between PySi and PySiOH importantly differs, being the former electron donor, as Py and N-PrPy. Conversely, PySiOH presents donor-acceptor character with LUMO energy level localized on the silanol end-group.Global and local reactivity descriptors predict PySiOH more reactive than PySi with two preferential reactive sites: electron-rich Py ring and electron-deficient silanol group. Based on experimental studies, oligomers of PySiOH linked α−α' via Py rings (α−α'Py n SiOH, n = 2,3) were considered as model molecules of hydrolyzed PySi. The most stable structures were derived from randomly generated α−α'Py n SiOH that were optimized at semiempirical AM1 and refined with M05-2X/6-31G(d,p). Conformational analysis of dimer and trimer structures points to stability enhanced by molecular packing. Nonetheless, NBO and RDG results indicate that oligomers stability is dictated by the cooperative contribution of hydrogen bonding between silanol end-groups and dispersive vdW interactions between silanol and the π system of Py ring.The latter interaction resulting from electron delocalization induced by electron deficient silanol group seems to determine the smaller gap energy of T-shaped OH-π arrangements. The theoretical findings support the peculiar chemical behavior revealed by experiment.

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“…To analyze whether the imidazole-NO complexes behave similarly, we performed a similar analysis for the Imi-NO dimers previously studied by us [30] ( These results suggest that the unpaired electron plays an important role on the stabilization of hydrogen by us, [4,5] where the unpaired electron did not affect significantly the stabilization of the complexes. The distinct behavior of NO can be explained considering the energy ordering of the NO orbitals.…”

Section: Is the Unpaired Orbital Of No Involved In Complex Formation?mentioning

confidence: 99%

“…[12][13][14][15][16] The dimerization of NO [17] as well as its interactions with small molecules like N 2 , CO, H 2 O, CH 4 , C 2 H 6 , C 6 H 6 , imidazole and amino acids were also investigated. [18][19][20][21][22][23][24][25][26][27][28][29][30] Weinhold et. al examined the complexes between NO and HF using the donor-acceptor scheme based on the Natural Bond Orbitals (NBO).…”

Section: Introductionmentioning

confidence: 99%

Complexes of nitric oxide with water and imidazole

et al. 2015

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NO-Imi-H 2 O complexes can be used as a model to investigate the interactions of histidine with nitric oxide and water in biological systems like myoglobin. We discuss here the water-imidazole, water-nitric oxide dimers and the trimolecular complexes of nitric oxide with water and imidazole from the donor-acceptor point of view using the Natural Bond Orbitals (NBO) and Energy Decomposition Analysis (EDA) schemes. The comparison between trimolecular and bimolecular complexes shows that in general, the stabilization energies are more sensitive to changes in the interactions of imidazole with water than to changes in the interactions with nitric oxide. The effect of imidazole ring protonation on the geometry and stabilization of the complexes is also investigated. We found that cooperative effects are more relevant in charged complexes and planar structures than in neutral species and non-planar complexes. The driving forces governing the interactions between open and closed shell systems are also discussed with special emphasis on the role of lone pairs and unpaired electrons.

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Exploring the potential energy surfaces of association of NO with aminoacids and related organic functional groups: the role of entropy of association

Cited by 11 publications

References 25 publications

Theoretical Study of Imidazole···NO Complexes

Theoretical Study of Imidazole···NO Complexes

Pyrrolyl–Silicon Compounds as Precursors for Donor–Acceptor Systems Stabilized by Noncovalent Interactions

Complexes of nitric oxide with water and imidazole

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