Far infra-red spectra and the molecular complexes of carbon tetrachloride and chloroform with benzene

Chantry, G.W.; Gebbie, H. A.; Mirza, Humza

doi:10.1016/0584-8539(67)80167-3

Cited by 13 publications

(5 citation statements)

References 3 publications

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“…Studies on the formation of 1:1 and 2:1CCl 4 -C 6 H 6 CTC were carried out previously by several authors. [6][7][8][9] In the current study the formation of CTC between carbon tetrachloride (CCl 4 ) and benzene (C 6 H 6 ) is confirmed by new evidence.…”

Section: Formation Of the Charge Transfer Complexsupporting

confidence: 54%

“…formed in reaction (6) abstracts a hydrogen atom from C 6 H 6 Cl . , formed according to reaction (7), as follows:…”

Section: Dependence Of the Chlorobenzene Concentration On Benzene Molmentioning

confidence: 99%

“…5 The formation of CTC was proposed between carbon tetrachloride and benzene with different molar ratios including 1:1 and 2:1. [6][7][8][9] g-Radiolysis of carbon tetrachloride has been studied in solutions of different solvents, 10,11 as well as in the pure state. 12,13 Pulse radiolysis of carbon tetrachloride was also carried out.…”

Section: Introductionmentioning

confidence: 99%

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Charge Transfer Complex Role in the Formation of Chlorobenzene in the γ‐Irradiated Carbon Tetrachloride‐Benzene System

Sife-Eldeen

Ebraheem

2007

J Chinese Chemical Soc

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The formation of carbon tetrachloride‐benzene charge transfer complex was confirmed by UV and NMR spectrometric studies. A change in UV spectrum of benzene is observed upon addition of carbon tetrachloride. Whereas the appearance of new bands supports the formation of charge transfer complex. NMR study shows that, chemical shift of benzene pmr signal depends on the CCl4‐C6H6 molar ratio. This observation is another criterion for the formation of benzene‐carbon tetrachloride charge transfer complex. Job's Continuous Variation method indicates that a 2:1 CCl4‐C6H6 charge transfer complex (2:1 CTC) is formed. The association constants (K2:1) of (2:1 CTC) was found to be 0.0197 M−2. The maximum concentration of (2:1 CTC) was found to be in samples with 2:1 CCl4‐C6H6 molar ratio (33% benzene mole). On the other hand the maximum yield of chlorobenzene was obtained, also, upon radiolysis of CCl4‐C6H6 samples at a 2:1 molar ratio (33% benzene mole). Therefore, it could be concluded that (2:1 CTC) participates in the formation of chlorobenzene upon radiolysis of the benzene‐carbon tetrachloride system. This conclusion was supported by the dependence of the chlorobenzene yield of a γ‐irradiated carbon tetrachloride‐benzene system (2:1 molar ratio) on irradiation time according to a third order kinetic equation with a very good linearity (R2 = 0.9977). Accordingly, the rate constant for the chlorobenzene formation under this condition was found to be ≈ 5.5 × 10−7 L2.mol−2.h−1. We propose a radiation chemical mechanism in which the 2:1 CTC plays a role in the formation of chlorobenzene.

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Section: Formation Of the Charge Transfer Complexsupporting

confidence: 54%

“…formed in reaction (6) abstracts a hydrogen atom from C 6 H 6 Cl . , formed according to reaction (7), as follows:…”

Section: Dependence Of the Chlorobenzene Concentration On Benzene Molmentioning

confidence: 99%

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Charge Transfer Complex Role in the Formation of Chlorobenzene in the γ‐Irradiated Carbon Tetrachloride‐Benzene System

Sife-Eldeen

Ebraheem

2007

J Chinese Chemical Soc

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“…To systematically develop the charge-transfer (CT) motif for the crystal engineering of stable diamondoid networks, we wish to now focus on the utilization of carbon tetrabromide (CBr 4 ) as the simplest (tetrahedral) building element. Indeed, this prototypical electron acceptor forms intermolecular complexes with one-dimensional donors, the charge-transfer nature of which has been revealed in a series of physical-chemical studies . Although the isolation of crystalline solids met significant difficulties due to the relatively low free energy of the complex formation, we earlier found stronger charge-transfer complexes of CBr 4 using better electron donors, especially tertiary aliphatic amines .…”

Section: Introductionmentioning

confidence: 84%

The Charge-Transfer Motif in Crystal Engineering. Self-Assembly of Acentric (Diamondoid) Networks from Halide Salts and Carbon Tetrabromide as Electron-Donor/Acceptor Synthons

2003

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Unusual strength and directionality for the charge-transfer motif (established in solution) are shown to carry over into the solid state by the facile synthesis of a series of robust crystals of the [1:1] donor/acceptor complexes of carbon tetrabromide with the electron-rich halide anions (chloride, bromide, and iodide). X-ray crystallographic analyses identify the consistent formation of diamondoid networks, the dimensionality of which is dictated by the size of the tetraalkylammonium counterion. For the tetraethylammonium bromide/carbon tetrabromide dyad, the three-dimensional (diamondoid) network consists of donor (bromide) and acceptor (CBr(4)) nodes alternately populated to result in the effective annihilation of centers of symmetry in agreement with the sphaleroid structural subclass. Such inherently acentric networks exhibit intensive nonlinear optical properties in which the second harmonics generation in the extended charge-transfer system is augmented by the effective electronic (HOMO-LUMO) coupling between contiguous CBr(4)/halide centers.

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“…Other evidence for such n-o interactions between aromatic compounds and CCI, comes from enthalpies of mixing (28), far i.r. spectra (29), and submillimeter dielectric absorption of mixtures (30), among many other measurements.…”

Section: / High F R E Q U E N C Y C O M P O N E N T J070mentioning

confidence: 99%

Infrared Absorption Band Shape Studies: Fundamental OH Stretching Vibration of Benzyl Alcohol Conformers in Dilute Carbon Tetrachloride Solution

Krueger¹,

Hawkins²

1973

Can. J. Chem.

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The fundamental OH stretching doublet in the i.r. spectra of a seriesof monomericp-X-benzyl alcohols (X = OCH,, CH,, H, C1, NOz) observed in dilute CCI, solution over the temperature range -5 to +40 "C is resolved into two components corresponding to different molecular conformers, using digital computing techniques and a Cauchy-Gauss sum band n~odel. The temperature and substituent dependence of frequencies, band shape indices, and band widths are discussed in terms of intranlolecular (electronic displacements and OH...n hydrogen bonds) and intermolecular (OH...CI,C and n-o electron donor-acceptor) interactions. The O H band shapes, which range from 60-98% Cauchy character, reflect variations in the intern~olecular interactions which impede molecular re-orientation, and c a n be correlated with the electronic nature of X and the molecular conformation. T h e formation of an intramolecular OH...n hydrogen bond results in significantly slower rotational relaxation of the alcohol molecule.The enthalpy differences between the two conformers are found to be 1.52 + 0.13, 1.57 + 0.15, 1.53 + 0.08, 1.06 + 0.13, and 1.15 + 0.1 1 kcal/mol for the compounds in the order stated above.Le doublet de la vibration fondamentale dlClongation du OH dans les spectres i.r. d'une sCrie d'alcools p-X-benzyliques monomeres (X = OCH,, CH,, H, C1, NOz) observe en solution diluCe dans CCI,, dans l'intervalle de temperature -5 a +40 "C, a t t e rtsolu en deuxcomposantes correspondant aux differentes conformations moleculaires par les techniques de calcul digital et sur un modele de sommation de bande selon Cauchy-Gauss. Les variations des frtquences en fonction de la temperature, substituant, indices de forme et largeurs de bande, ont ete discutees par rapport aux interactions intramolCculaires (dkplacement electronique et liaisons hydrogene OH...n) et intermolCculaires (OH...CI,C et n-o donneur-accepteur d'electron). Les formes des bandes O H qui ont un caractere de Cauchy de 60 2 98%, refletent les variations des interactions intermolCculaires qui genent la rdorientation molCculaire et peuvent &tre en correlation avec la nature electronique de X et la conformation molCculaire. La formation d'une liaison hydrogene intramoleculaire OH...n a pour r e s~~l t a t Line relaxation rotationnelle nettement plus lente pour la molCcule alcool. Les differences d'enthalpie entre les deux conformeres sont de 1.52 + 0.13, 1.57 +_ 0.15, 1.53 + 0.08, 1.06 + 0.13 et 1.15 + 0.1 1 kcal/mol pour les composks dans I'ordre cite ci-dessus.

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Far infra-red spectra and the molecular complexes of carbon tetrachloride and chloroform with benzene

Cited by 13 publications

References 3 publications

Charge Transfer Complex Role in the Formation of Chlorobenzene in the γ‐Irradiated Carbon Tetrachloride‐Benzene System

Charge Transfer Complex Role in the Formation of Chlorobenzene in the γ‐Irradiated Carbon Tetrachloride‐Benzene System

The Charge-Transfer Motif in Crystal Engineering. Self-Assembly of Acentric (Diamondoid) Networks from Halide Salts and Carbon Tetrabromide as Electron-Donor/Acceptor Synthons

Infrared Absorption Band Shape Studies: Fundamental OH Stretching Vibration of Benzyl Alcohol Conformers in Dilute Carbon Tetrachloride Solution

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