3-Nitrocinnamic acid

doi:10.1107/S1600536805031879

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3-Nitrocinnamic acid

Journal Article•DOI•

3-Nitrocinnamic acid

K. Udaya Lakshmi¹, Subbiah Thamotharan², M. Srinivasan³, K. Ramamurthi¹, Babu Varghese³ - Show less +1 more•Institutions (3)

Bharathidasan University¹, Indian Institute of Science², Indian Institute of Technology Madras³

01 Nov 2005-Acta Crystallographica Section E-structure Reports Online (Blackwell Publishing)-Vol. 61, Iss: 11

TL;DR: The title compound, $C_{9}H_{7}NO_{4} as discussed by the authors, forms centrosymmetric dimers through intermolecular O-(HO)-O-... hydrogen bonds in the crystal structure.

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Abstract: The title compound, $C_{9}H_{7}NO_{4}$, forms centrosymmetric dimers through intermolecular O-(HO)-O-... hydrogen bonds in the crystal structure.The nitro group deviates slightly from coplanarity with the benzene ring. The benzene ring and the carboxylic acid group are in an E configuration about the ethylenic double bond.

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Journal Article•DOI•

Polymorphism in a trans-Cinnamic Acid Derivative Exhibiting Two Distinct β-type Phases: Structural Properties, [2 + 2] Photodimerization Reactions, and Polymorphic Phase Transition Behavior

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Manal A. Khoj¹, Colan E. Hughes¹, Kenneth D. M. Harris¹, Benson M. Kariuki¹•Institutions (1)

Cardiff University¹

02 Aug 2013-Crystal Growth & Design

TL;DR: In this paper, a rare case of polymorphism among trans-cinnamic-β-truxinic derivatives in which both polymorphs are classified as β-type structures based on their solidstate structural properties and their solid-state photoreactivity was reported.

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Abstract: We report the discovery of a rare case of polymorphism among trans-cinnamic acid derivatives in which both polymorphs are classified as β-type structures based on their solidstate structural properties and their solid-state photoreactivity. Specifically, for 3-fluoro-transcinnamic acid, crystallization from many solvent systems leads to formation of one polymorph (denoted β1), although, in a few cases, concomitant crystallization of another polymorph (denoted β2) is also observed. On heating the β1 polymorph, a solid-state phase transition occurs at ca. 119 °C to produce the β2 polymorph. This polymorphic phase transition is irreversible, and the β2 polymorph remains stable on subsequent cooling to ambient temperature. Both the β1 and the β2 polymorphs undergo a topochemical [2 + 2] photodimerization reaction upon UV irradiation to produce 3,3′- difluoro-β-truxinic acid as the photoproduct in almost 100% yield. However, these reactions are associated with complete loss of crystallinity, preventing the structural properties of the directly produced solid photoproduct from being determined by singlecrystal or powder X-ray diffraction techniques.

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27 citations

Journal Article•DOI•

Studies on crystal growth, vibrational, dielectric, electronic, mechanical and thermal properties of new organic nonlinear optical crystal: 3-nitrocinnamic acid

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S. Alen¹, S. Alen², D. Sajan¹, K. Job Sabu¹, K. Udaya Lakshmi³, V. Veeraiah, Kadali Chaitanya⁴, V. Bena Jothy² - Show less +4 more•Institutions (4)

Bishop Moore College¹, Women's Christian College, Chennai², Saveetha University³, Nanjing University of Science and Technology⁴

25 Oct 2013-CrystEngComm

TL;DR: In this paper, 3-Nitrocinnamic acid (3NCA) was synthesized and its crystals were grown in aqueous solution by slow evaporation solution growth technique.

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Abstract: 3-Nitrocinnamic acid (3NCA) was synthesized and its crystals were grown in aqueous solution by slow evaporation solution growth technique. The grown crystal was confirmed by powder XRD studies. The geometry, intermolecular hydrogen bonding, and harmonic vibrational wavenumbers of 3NCA were investigated with the help of B3LYP density functional theory (DFT) methods. The calculated molecular geometry has been compared with the experimental data obtained from XRD data. The assignments of the vibrational spectra have been carried out with the aid of normal coordinate analysis (NCA) following the scaled quantum mechanical force field methodology (SQMFF). Vibrational spectral investigation confirms the formation of cyclic dimers in the crystal, with the carboxyl groups of each acid molecule bonded to those of adjacent molecules. The red shift of the O–H stretching wavenumber is due to the formation of strong O–H⋯O hydrogen bonds by hyperconjugation between the carbonyl oxygen lone electron pairs and the O–H σ* antibonding orbitals. Thermal stability of the grown crystal was examined by recording TGA/DTA. Mechanical strength of the grown material was tested by hardness studies. Second harmonic frequency generation was examined by Kurtz and Perry powder test and it reveals that the relative conversion efficiency is 0.8 times greater than that of urea. The theoretical first order hyperpolarizability value was calculated for the optimized structure.

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16 citations

Journal Article•DOI•

Synthesis of Ph3Bi(O2CR)2 Compounds with Unsaturated Carboxylic Acids and Use of Triphenylbismuth Dicrotonate in the Synthesis of Bismuth-Containing Polymers

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01 Jan 2022-Russian Journal of General Chemistry

1 citations

Journal Article•DOI•

Synthesis of Ph3Sb(O2CR)2 Compounds with Unsaturated Carboxylic Acids and Use of Triphenylantimony Dicrotonate for the Production of Sb-Containing Polymers

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Aleksey V. Gushchin¹•Institutions (1)

N. I. Lobachevsky State University of Nizhny Novgorod¹

01 Feb 2023-Russian Journal of General Chemistry

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Journal Article•DOI•

ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI)

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Louis J. Farrugia¹•Institutions (1)

University of Glasgow¹

01 Oct 1997-Journal of Applied Crystallography

TL;DR: L Lists of software presented and~or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known.

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Abstract: Computer Program Abstracts The category Computer Program Abstracts provides a rapid means of communicating up-to-date information concerning both new programs or systems and significant updates to existing ones. Following normal submission, a Computer Program Abstract will be reviewed by one or two members of the IUCr Commission on Crystallographic Computing. It should not exceed 500 words in length and should follow the standard format given on page 189 of the June 1985 issue of the Journal [J. Appl. CrysL (1985). 18, 189190] and on the World Wide Web at http://www.iucr. ac. uk/journals/jac/software/. Lists of software presented and~or reviewed in the Journal of Applied Crystallography are available on the World Wide Web at the above address, together with information about the availability of the software where this is known. J. App/. CrysL (1997). 30, 565 ORTEP-3 for Windows a version of ORTEP-III with a Graphical User Interface (GUI)

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19,468 citations

"3-Nitrocinnamic acid" refers methods in this paper

...…MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003)....
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...Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003)....
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Journal Article•DOI•

Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals

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Joel Bernstein¹, Joel Bernstein², Raymond E. Davis¹, Liat Shimoni², Ning-Leh Chang¹ - Show less +1 more•Institutions (2)

University of Texas at Austin¹, Ben-Gurion University of the Negev²

18 Aug 1995-Angewandte Chemie

TL;DR: In this article, a review of the most promising systematic approaches to resolving this enigma was initially developed by the late M. C. Etter, who applied graph theory to recognize, and then utilize, patterns of hydrogen bonding for the understanding and design of molecular crystals.

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Abstract: Whereas much of organic chemistry has classically dealt with the preparation and study of the properties of individual molecules, an increasingly significant portion of the activity in chemical research involves understanding and utilizing the nature of the interactions between molecules. Two representative areas of this evolution are supramolecular chemistry and molecular recognition. The interactions between molecules are governed by intermolecular forces whose energetic and geometric properties are much less well understood than those of classical chemical bonds between atoms. Among the strongest of these interactions, however, are hydrogen bonds, whose directional properties are better understood on the local level (that is, for a single hydrogen bond) than many other types of non-bonded interactions. Nevertheless, the means by which to characterize, understand, and predict the consequences of many hydrogen bonds among molecules, and the resulting formation of molecular aggregates (on the microscopic scale) or crystals (on the macroscopic scale) has remained largely enigmatic. One of the most promising systematic approaches to resolving this enigma was initially developed by the late M. C. Etter, who applied graph theory to recognize, and then utilize, patterns of hydrogen bonding for the understanding and design of molecular crystals. In working with Etter's original ideas the power and potential utility of this approach on one hand, and on the other, the need to develop and extend the initial Etter formalism was generally recognized. It with that latter purpose that we originally undertook the present review.

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7,616 citations

Additional excerpts

...2) (Bernstein et al., 1995)....
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Journal Article•DOI•

SIRPOW.92 – a program for automatic solution of crystal structures by direct methods optimized for powder data

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Angela Altomare, Giovanni Luca Cascarano, C. Giacovazzo, Antonietta Guagliardi, Maria Cristina Burla, Giampiero Polidori, Mercedes Camalli - Show less +3 more

01 Jun 1994-Journal of Applied Crystallography

6,902 citations

Journal Article•DOI•

A semi-empirical method of absorption correction

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A. C. T. North, D. C. Phillips, F. S. Mathews

01 May 1968-Acta Crystallographica Section A

TL;DR: An extension of Furnas's method is described in this paper, where the variation of intensity of an axial reflection as the crystal is rotated about the goniometer axis is used to give a curve of relative transmission T against azimuthal angle ϕ for the corresponding reciprocal lattice level.

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Abstract: An extension of Furnas's method is described. The variation of intensity of an axial reflection as the crystal is rotated about the goniometer axis is used to give a curve of relative transmission T against azimuthal angle ϕ for the corresponding reciprocal lattice level. Transmission coefficients for any general reflexion hkl are then given approximately by T(hkl) = [T(ϕinc) + T(ϕret)]/2 where ϕinc and ϕret are the azimuthal angles of the incident and reflected beams. Equations are derived for (ϕinc and ϕret and the accuracy of the method is discussed.

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6,872 citations

"3-Nitrocinnamic acid" refers background in this paper

...Enraf–Nonius CAD-4 diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω–2θ scans Absorption correction: ψ scan (North et al., 1968) Tmin = 0.751, Tmax = 0.823 1733 measured reflections 1478 independent reflections 1068 reflections with I > 2σ(I) Rint = 0.043 θmax =…...
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...–2 scans Absorption correction: scan (North et al., 1968) Tmin = 0.751, Tmax = 0.823 1733 measured reflections 1478 independent reflections 1068 reflections with I > 2 (I) Rint = 0.043 max = 67.9 h = 0!...
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Journal Article•DOI•

SIR92 – a program for automatic solution of crystal structures by direct methods

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Angela Altomare, Giovanni Luca Cascarano, C. Giacovazzo, Antonietta Guagliardi, Maria Cristina Burla, Giampiero Polidori, Mercedes Camalli - Show less +3 more

01 Jun 1994-Journal of Applied Crystallography

6,216 citations

"3-Nitrocinnamic acid" refers methods in this paper

...Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003)....
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...…CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP3 for Windows (Farrugia, 1997);…...
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