Structure of the Solid Compound Formed by Addition of Two Molecules of Iodine to One Molecule of Pyridine.

Hassel, O.; Hope, H.; Sørensen, Nils Andreas; Dam, Henrik Friis; Sjöberg, Berndt; Toft, Jens

doi:10.3891/acta.chem.scand.15-0407

Cited by 116 publications

(72 citation statements)

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“…Several attempts to model the separate pivoting motions of the rings in terms of twofold positional disorder were only partially successful, indicating that the complexity of the dynamic disorder in this crystal resists a simple treatment. The best attempt to resolve the disorder, by splitting the C(32) and C (33) positions and those of all six cation carbons (Tables A-C) produced an overall improvement (Table 2) and significantly lowered the largest Uii in both the anion and the cation.…”

Section: Msotbmentioning

confidence: 99%

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Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me₃S⁺,Et₃S⁺,Me₃SO⁺,Ph₂I⁺, and 1-azoniapropellane tetraphenylborates

Knop¹,

Cameron²,

Bakshi³

et al. 1994

Can. J. Chem.

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Determination of the crystal structures of the tetraphenylborates of the trimethylsulfonium (Me3S+,P21/n), triethylsulfonium (Et3S+,Cmcm), trimethylsulfoxonium (Me3SO+,P21/m), diphenyliodonium (Ph2I+,Pnma), and 1-azoniapropellane (C10H18N+,P21/n) cations has shown that when regions of high local electron density (lone electron pairs) are present in the cation, the cation orients itself so as to minimize the repulsion between the lone pair(s) and the nearest anion phenyl groups, i.e. the cation orientation responds to the lone pair – aromatic π system interaction. This behaviour contrasts with the formation of H …π hydrogen bonds in tetraphenylborates of organic ammonium cations containing N-hydrogens and provides corroborative evidence for our previous finding: (1) given the opportunity, a cation N-hydrogen will form a hydrogen bond to a phenyl group(s) of the anion; (2) the orientation of the cation to form the N—H(N) …π bond is thus a manifestation of a positive hydrogen-bonding tendency rather than a passive response to overall packing requirements in the crystal. The geometries of the above cations are compared to those reported in the literature and those of Me3S+ and Me3SO+ have also been optimized by ab initio (RHF/6-31G*) methods.

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Section: Msotbmentioning

confidence: 99%

“…10) values on C(32) and C (33). Seeking to minimize the repulsion between H(32) and H(4)' (and between the symmetry counterparts of these hydrogens, Fig.…”

Section: Msotbmentioning

confidence: 99%

Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me₃S⁺,Et₃S⁺,Me₃SO⁺,Ph₂I⁺, and 1-azoniapropellane tetraphenylborates

Knop¹,

Cameron²,

Bakshi³

et al. 1994

Can. J. Chem.

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“…We have employed electrochemical cells of the following types [13] Pt/12, NaI(c) in P~/ / I~, Na1(c1) in Py IPt and We will assume that added NaI or TEAI, represented by the term MI, is completely ionized according to the reactions and [16] MI + Py21+ -+ PyI'I-+ F'y + M+ complete ionization of MI appears reasonable on the basis of the known information about the ionization of NaI and TEAI and the stability of I; (11,14). The species PyI+IP, Py21+, and I3 rapidly resume thermodynamic equilibrium on the basis of reaction [4].…”

Section: Electrochemical Equationsmentioning

confidence: 99%

Ionic dissociation in pyridine–iodine solutions

Aronson¹,

Wilensky²,

Yeh³

et al. 1986

Can. J. Chem.

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An electrochemical technique has been employed to study the ionization of the pyridine-iodine complex in pure pyridine and in 1,2-dichloroethane. A mechanism for the ionization in accord with the experimental data is proposed. The results indicate that, for wide ranges of iodine and pyridine concentration, one quarter of the I2 is dissociated into ionic species.SEYMOUR ARONSON, STUART BRYAN WILENSKY, TAUN-IUAN YEH, DARNEL DEGRAFF et GRACE MARILYN WIEDER. Can. J. Chem. 64, 2060Chem. 64, (1986.OpCrant dans la pyridine pure ainsi que dans le dichloro-1,2 Cthane, on a utilist une technique Clectrochimique pour ttudier l'ionisation du complexe pyridine/iode. On propose un mCcanisme pour l'ionisation qui est en accord avec les donnCes expCrimentales. Les rCsultats indiquent que, pour des concentrations trks variables d'iode et de pyridine, 25% du I2 est dissociC en espkces ioniques.[Traduit par la revue]

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“…Even though the two cations display such different conformations, the three unique I-N distances are similar and have an average value of 2.29A. The corresponding distance in pyridine.2I 2 is 2.16 A (Hassel & Hope, 1961) and for the bis(3-picolyl)iodonium cation it is 2.24 A (Osborn, 1972). It has been suggested that these latter two distances are shorter than those observed for tertiary amines; e.g.…”

mentioning

confidence: 99%

“…A linear or nearly linear bond angle at the iodine has been observed frequently; for example 180 ° in the dipyridyliodonium cation (Hassel & Hope, 1961), 179 ° in pyridine.IC1 (Romming, 1972), 180 ° in 4-picoline.I 2 (Hassel, Romming & Tufte, 1961), 176 ° in trimethylamine.IC1 (Hassel & Hope, 1960), 180 ° in trimethylamine.I 2 (Stromme, 1959) and 176.5 ° in bis(hexamethylenetetramine)iodonium triiodide (Pritzkow, 1975). A partial packing diagram is shown in Fig.…”

mentioning

confidence: 99%

A charge-transfer complex: bis(2,4,6-trimethyl-1-pyridyl)iodonium perchlorate

Brayer¹,

James²

1982

Acta Crystallogr Sect B

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Structure of the Solid Compound Formed by Addition of Two Molecules of Iodine to One Molecule of Pyridine.

Cited by 116 publications

References 0 publications

Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me₃S⁺,Et₃S⁺,Me₃SO⁺,Ph₂I⁺, and 1-azoniapropellane tetraphenylborates

Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me₃S⁺,Et₃S⁺,Me₃SO⁺,Ph₂I⁺, and 1-azoniapropellane tetraphenylborates

Ionic dissociation in pyridine–iodine solutions

A charge-transfer complex: bis(2,4,6-trimethyl-1-pyridyl)iodonium perchlorate

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Structure of the Solid Compound Formed by Addition of Two Molecules of Iodine to One Molecule of Pyridine.

Cited by 116 publications

References 0 publications

Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me3S+,Et3S+,Me3SO+,Ph2I+, and 1-azoniapropellane tetraphenylborates

Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me3S+,Et3S+,Me3SO+,Ph2I+, and 1-azoniapropellane tetraphenylborates

Ionic dissociation in pyridine–iodine solutions

A charge-transfer complex: bis(2,4,6-trimethyl-1-pyridyl)iodonium perchlorate

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Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me₃S⁺,Et₃S⁺,Me₃SO⁺,Ph₂I⁺, and 1-azoniapropellane tetraphenylborates

Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me₃S⁺,Et₃S⁺,Me₃SO⁺,Ph₂I⁺, and 1-azoniapropellane tetraphenylborates