Molecular Cocrystals of Carboxylic Acids. XXVII An Investigation into the Use of Triphenylphosphine Oxide Cocrystals for Non-Linear Optics: the Crystal Structure of the Adduct of Triphenylphosphine Oxide with N-Methylpyrrole-2-carboxylic Acid

1997 ◽  
Vol 50 (12) ◽  
pp. 1191 ◽  
Author(s):  
Daniel E. Lynch, ◽  
Graham Smith ◽  
Karl A. Byriel, ◽  
Colin H. L. Kennard, ◽  
Johann Kwiatkowski ◽  
...  

Four adducts of triphenylphosphine oxide with aromatic carboxylic acids have been synthesized and tested for second-order non-linear optical properties. These were with N-methylpyrrole-2-carboxylic acid (1), indole-2-carboxylic acid (2), 3-dimethylaminobenzoic acid (3), and thiophen-2-carboxylic acid (4). Compound (1) produced clear, colourless crystals (space group P 212121 with a 9·892(1), b 14·033(1), c 15·305(1) Å, Z 4) which allowed the structure to be determined by X-ray diffraction.

2000 ◽  
Vol 55 (8) ◽  
pp. 677-684 ◽  
Author(s):  
Maciej Kubicki ◽  
Teresa Borowiak ◽  
Wiesław Z. Antkowiak

Abstract The tendency of forming mixed carboxyl-to-oxime hydrogen bonds was tested on the series of bornane derivatives: one with the acid function only (bornane-2-endo-carboxylic acid), one with the oxime function (2,2′-diethylthiobomane-3-oxime), and one with both oxime and carboxylic functions (bornane-2-oxime-3-endo-carboxylic acid). The crystal structures of these compounds were determined by means of X-ray diffraction. In bornane-2-endo-carboxylic acid and 2,2′-diethylthiobornane-3-oxime 'homogenic' hydrogen bonds were found, and these hydrogen bonds close eight-and six-membered rings, respectively. By contrast, in bornane-2-oxime-3-endo-carboxylic acid 'heterogenic' hydrogen bonds between carboxylic and oxime bonds were found. This carboxylic-oxime, or 'carboxyoxime' system is almost always present in compounds which have both oxime and carboxylic groups; therefore it can be regarded as an element of supramolecular structures (synthon). The presence of such synthons can break the tendency of carboxylic acids and oximes towards crystallizing in centrosymmetric structures.


1983 ◽  
Vol 36 (12) ◽  
pp. 2455 ◽  
Author(s):  
G Smith ◽  
CHL Kennard ◽  
GF Katekar

The crystal structures of three geotropically active phthalamic acid derivatives have been determined by means of X-ray diffraction and the structural systematics for the series compared. The three acids are conformationally similar and, in contrast to the tendency among carboxylic acids to form hydrogen-bonded dimers, they exist as monomers with intermolecular hydrogen bonding between the carboxylic acid groups and the nitrogen or oxygen of the amide side chains.


1998 ◽  
Vol 51 (11) ◽  
pp. 1019 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard

Five adducts consisting of carboxylic acid-substituted indoles with nitro-substituted benzoic acids have been synthesized and tested for second-order non-linear optical properties. These were indole-2-carboxylic acid with 2,4-dinitrobenzoic acid (1), 3,5-dinitrobenzoic acid (2), and 2,4,6-trinitrobenzoic acid (3), and indole-3-acetic acid with 3,5-dinitrobenzoic acid (4), and 2,4,6-trinitrobenzoic acid (5). Compound (2) produced clear, yellow crystals (space group P -1 with a 6·8400(7), b 15·150(2), c 16·097(2) Å, α 84·911(9), β 87·088(10), γ 77·865(9)°, Z 4) which allowed the structure to be determined by X-ray diffraction. Of the five adducts, compounds (3) and (5) gave second harmonic intensities of 0·15 and 0·16 times respectively that of a urea standard.


1998 ◽  
Vol 51 (9) ◽  
pp. 813 ◽  
Author(s):  
Daniel E. Lynch ◽  
Niraj Mistry ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard

The molecular adducts of indole-3-acetic acid (iaa) and indole-2-carboxylic acid (ica) with 5-nitroquinoline (nq), [(iaa)(nq)2] (1) and [(ica)(nq)] (2), have been prepared and characterized by X-ray diffraction and spectroscopic methods. Both examples involve charge transfer as well as a network of hydrogen-bonding interactions. Thin films of compound (2), and other similar adduct complexes of ica, can be prepared by thermal evaporation techniques and in this form exhibit a weak second-order non-linear optical signal. However, these films display poor optical quality and, without improvement, are not suitable for any potential non-linear optical applications.


2015 ◽  
Vol 3 (5) ◽  
pp. 1099-1105 ◽  
Author(s):  
Liang Liu ◽  
Shai Yellinek ◽  
Noam Tal ◽  
Reut Toledano ◽  
Ariela Donval ◽  
...  

This work reports a method for electrodepositing sol–gel/CNT composite films. The deposition is highly selective to conductive surfaces, and the films exhibit non-linear optical properties and excellent antireflection performance.


1992 ◽  
Vol 45 (6) ◽  
pp. 969 ◽  
Author(s):  
KA Byriel ◽  
CHL Kennard ◽  
DE Lynch ◽  
G Smith ◽  
JG Thompson

The cocrystal adducts of a number of carboxylic acids with organic heterocyclic bases have been prepared, and their structures and intermolecular interactions interpreted through X-ray diffraction and infrared spectroscopic techniques. The crystal structures of three of these compounds, the 1 : 1 adducts [{(2,4-dich1orophenoxy)acetic acid)(3-hydroxypyridine)] (1), [(2,4,6-trinitrobenzoie acid)(2-aminopyrimidine)] (2), and [(4-nitrobenzoic acid)(3-amino- 1,2,4-trimole)] (3), have been determined by single-crystal X-ray diffraction and refined to residuals R 0.026, 0.033 and 0.040 for 1814, 1531 and 727 observed reflections, respectively.


1998 ◽  
Vol 51 (5) ◽  
pp. 403 ◽  
Author(s):  
Daniel E. Lynch ◽  
Tariq Latif ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard ◽  
...  

A series of molecular adducts of 2-aminopyrimidine and 3-amino-1,2,4-triazole with heterocyclic carboxylic acids have been prepared and characterized by using X-ray powder diffraction and in four cases by single-crystal X-ray diffraction methods. These four compounds are the (1 : 1) adducts of 2-aminopyrimidine with indole-3-acetic acid [(C4H5N3)(C10H9NO2)], N-methylpyrrole-2-carboxylic acid [(C4H5N3)(C6H7NO2)] and thiophen-2-carboxylic acid [(C4H5N3)(C5H4O2S)], and the (1 : 1) adduct of 3-amino-1,2,4-triazole with thiophen-2-carboxylic acid [(C2H4N4)(C5H4O2S)]. Other compounds described are the (1 : 1) adducts of 3-amino-1,2,4-triazole with indole-3-acetic acid and N-methylpyrrole-2-carboxylic acid.


1976 ◽  
Vol 30 (2) ◽  
pp. 204-209 ◽  
Author(s):  
Kenneth J. Garska

In order to extend the data available for the characterization of carboxylic acids, an x-ray diffraction technique has been used for the identification of their anilide derivatives. This technique often makes possible the identification of carboxylic acids that cannot be examined readily by other techniques such as gas chromotography and mass spectrometry. Reference x-ray diffraction patterns have been obtained for the anilide derivatives of 32 carboxylic acids containing up to 18 carbon atoms. Detailed descriptions are given for obtaining and qualitatively using the x-ray diffraction patterns of these anilides. The x-ray diffraction patterns of these anilides are unique; even closely related acids which differ only in isomeric form produce anilide derivatives which exhibit different and characteristic x-ray diffraction patterns. In the qualitative analysis of single or multicomponent carboxylic acid-containing mixtures, this x-ray diffraction technique is used either alone or with infrared spectrometric techniques.


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