Statistical analysis of noncovalent interactions of anion groups in crystal structures. II. Hydrogen bonding of thiocyanate anions

Tchertanov, Luba; Pascard, Claudine

doi:10.1107/s0108768196003011

Cited by 21 publications

(17 citation statements)

References 10 publications

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“…For this comparison, we used the most recent version of the CSD (April, 1996). Therefore, the numbers of retrieved fragments of discrete thiocyanate reported here differ slightly from those in our previous paper (Tchertanov & Pascard, 1996). The data reported here for the discrete anion only concern multiple hydrogen-bonding properties.…”

Section: Hydrogen Bonding To Metal-coordinated Isothiocyanates and Thcontrasting

confidence: 80%

“…In an earlier report we analysed the hydrogen bonding of discrete thiocyanate anions (Tchertanov & Pascard, 1996). We now extend the study of the hydrogen-bonding capability of free (SCN)-to that of the metal-bonded anion in order to see if the hydrogenbond acceptor properties of (SCN)-are modified by coordination through one terminal atom.…”

Section: Introductionmentioning

confidence: 93%

“…The most important observations resulting from the previous analysis of hydrogen bonding of discrete thiocyanate ions (Tchertanov & Pascard, 1996) can be summarized here. Thiocyanate is able to accept all types of hydrogen donors (oxygen and nitrogen).…”

Section: Hydrogen Bonding To Metal-coordinated Isothiocyanates and Thmentioning

confidence: 99%

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Statistical Analysis of Noncovalent Interactions of Anion Groups in Crystal Structures. III. Metal Complexes of Thiocyanate and their Hydrogen-Donor Accepting Function

Tchertanov¹,

Pascard²

1997

Acta Crystallogr Sect B

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The bidentate function of the thiocyanate anion was studied using the Cambridge Structural Database System. Complexing properties (metal-thiocyanate interactions) with respect to metal cations were analysed. Two main classes were distinguished: (a) alkali and alkaline earth metals, and (b) metals of Zn and Cu groups and transition metals (group VIII). Good correlations were found between the nature of the metal (radius, oxidation state and charge) and its position relative to the thiocyanate unit. Hydrogen-bond acceptor properties of discrete and complexed SCN units were compared. The extraordinarily active hydrogenbonding behaviour allows this anion to act as a powerful bridge between different molecular fragments. In metal complexes the cation provokes a redistribution of anionic charge in SCN and the distribution of electron density, in turn, controls the hydrogen-bonding properties of the terminal acceptor atom. Binding properties of thiocyanate in biological systems were illustrated using the Brookhaven Protein Data Bank. A comparison of anion binding in small-molecule structures and in macromolecular structures shows good agreement.

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Section: Hydrogen Bonding To Metal-coordinated Isothiocyanates and Thcontrasting

confidence: 80%

Section: Introductionmentioning

confidence: 93%

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Statistical Analysis of Noncovalent Interactions of Anion Groups in Crystal Structures. III. Metal Complexes of Thiocyanate and their Hydrogen-Donor Accepting Function

Tchertanov¹,

Pascard²

1997

Acta Crystallogr Sect B

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“…Recently, Tchertanov & Pascard (1996) (hereafter referred to as TP96) studied hydrogen bonding to thiocyanate anions, using crystallographic data retrieved from the Cambridge Structural Database (CSD : Allen et aL, 1991). It was found that the average hydrogen-bond geometry around the sulfur acceptor atom is approximately perpendicular to the SCN axis (Os = L D...S--N ~ 100 °, D = N or O), whereas the average geometry of hydrogen-bond formation to the N atom was found to be at an angle of tgN = / D.…”

Section: Introductionmentioning

confidence: 99%

“…

AbstractA statistical analysis of entries from the CSD (Cambridge Structural Database) showed that the average hydrogen-bond geometry to the nitrogen acceptor atom of the thiocyanate anion was not collinear with respect to the molecular axis of the anion and so not collinear with the nitrogen lone pair [Tchertanov & Pascard (1996). Acta Cryst.

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confidence: 99%

Hydrogen Bonding to Thiocyanate Anions: Statistical and Quantum-Chemical Analyses

Lommerse¹,

Cole²

1998

Acta Crystallogr Sect B

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A statistical analysis of entries from the CSD (Cambridge Structural Database) showed that the average hydrogen-bond geometry to the nitrogen acceptor atom of the thiocyanate anion was not collinear with respect to the molecular axis of the anion and so not collinear with the nitrogen lone pair [Tchertanov & Pascard (1996). Acta Cryst. B52, 685-690]. This somewhat unexpected result has been investigated further using theoretical energy calculations applying Intermolecular Perturbation Theory in combination with a more detailed statistical analysis of an appropriate CSD dataset. The energy calculations pointed to the formation of the strongest hydrogen bonds in the nitrogen lone-pair direction. The statistical analysis showed that this directionality occurs in cases where the N atom accepts one hydrogen bond only. The non-linear average hydrogen-bond geometry observed in the earlier study can be attributed to multiple hydrogen bonding to the N atom. In such cases, there is a shift away from the optimum orientation.observed frequently (Legon & Millen, 1982;Taylor et al., 1983) and can be ascribed, primarily, to optimization of the electrostatic attraction which is the largest energy contribution to hydrogen-bond formation. It is difficult to draw a general conclusion from the study by Baranovskii et al. (1985), however, as water molecules appear to have special donor features by comparison with other (aliphatic) hydroxyl donors (Tse et al., 1980; Kroon-Bateburg & van Duijneveldt, 1986;Zheng & Merz, 1992). In theoretical calculations (Lommerse et al., 1997) ether O atoms accept water hydroxyl donors in the direction of one of their lone pairs, but methanol hydroxyl donors between their lone pairs. This paper presents a more detailed study of hydrogen bonding to thiocyanate anions. A further statistical survey of CSD information is presented which considers the effect of hydrogen-bond coordination on the mean hydrogen-bond geometry to thiocyanate anions. Theoretical energy calculations using Intermolecular Perturbation Theory (IMPT: Hayes & Stone, 1984) for a suitable model system are also presented.

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The Nature of Hydrogen Bonding in Protic Ionic Liquids

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Statistical analysis of noncovalent interactions of anion groups in crystal structures. II. Hydrogen bonding of thiocyanate anions

Cited by 21 publications

References 10 publications

Statistical Analysis of Noncovalent Interactions of Anion Groups in Crystal Structures. III. Metal Complexes of Thiocyanate and their Hydrogen-Donor Accepting Function

Statistical Analysis of Noncovalent Interactions of Anion Groups in Crystal Structures. III. Metal Complexes of Thiocyanate and their Hydrogen-Donor Accepting Function

Hydrogen Bonding to Thiocyanate Anions: Statistical and Quantum-Chemical Analyses

The Nature of Hydrogen Bonding in Protic Ionic Liquids

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