Publications by authors named "John Masnovi"

5 Publications

  • Page 1 of 1

Crystal structure of 9-methacryloylanthracene.

Acta Crystallogr E Crystallogr Commun 2015 Apr 11;71(Pt 4):357-9. Epub 2015 Mar 11.

Department of Chemistry, University of Akron, Akron OH 44325, USA.

In the title compound, C18H14O, with systematic name 1-(anthracen-9-yl)-2-methyl-prop-2-en-1-one, the ketonic C atom lies 0.2030 (16) Å out of the anthryl-ring-system plane. The dihedral angle between the planes of the anthryl and methacryloyl moieties is 88.30 (3)° and the stereochemistry about the Csp (2)-Csp (2) bond in the side chain is transoid. In the crystal, the end rings of the anthryl units in adjacent mol-ecules associate in parallel-planar orientations [shortest centroid-centroid distance = 3.6320 (7) Å]. A weak hydrogen bond is observed between an aromatic H atom and the O atom of a mol-ecule displaced by translation in the a-axis direction, forming sheets of parallel-planar anthryl groups packing in this direction.
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http://dx.doi.org/10.1107/S2056989015004090DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438842PMC
April 2015

Gaseous cation chemistry and chain-length effects in electron ionization and collision-induced dissociation mass spectra of symmetric 1,n-bis(9-anthracenyl)alkanes.

J Mass Spectrom 2011 Jun;46(6):572-86

Department of Chemistry, Youngstown State University, OH 44555, USA.

The behavior of the gaseous cations resulting from EI (30 and 70 eV) of the bichromophoric title compounds 1-5 (for n = 1-5, respectively) is examined by ion-trap mass spectrometry, including collision-induced dissociation (CID) with variation in collision energy. These results are compared with those from anthracene and 9-methylanthracene and with previously reported mass spectrometric results for 3 and dicarbazolylalkanes. Rather than using the kinetic method to obtain ion energetics where the fragmentation mechanism is clear, as commonly done, the method is used here with relative complementary-ion abundances from CID to test the proposed fragmentation mechanisms using B3LYP calculations of relative ionization energies and optimized geometries of ionic and neutral fragments. Hydrogen migrations are common, and skeletal rearrangements including formation of expanded, fused and spiro rings are proposed in several cases. Of the chain cleavages, α-homolysis giving C(15) H(11) (+) , likely as dibenzotropylium, is most important for each of 1-5 except 3, where β-cleavage to C(16) H(13) (+) dominates with a proposed methyldibenzotropylium structure. α-Cleavage was important also in the dicarbazolylalkanes. A previous inference of a McLafferty rearrangement to explain C(15) H(12) (+•) from 3 is not supported by the present results. The fragmentation behavior of 1-5 depends strongly on n and implies significant interchromophoric interaction between anthracenyl groups.
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http://dx.doi.org/10.1002/jms.1927DOI Listing
June 2011

Charge-transfer complexations of 1,n-di(9-ethylcarbazol-3-yl)alkanes with tetracyanoethylene and tetranitromethane.

Spectrochim Acta A Mol Biomol Spectrosc 2009 Jan 3;71(5):1973-8. Epub 2008 Aug 3.

Balikesir University, Necatibey Faculty of Education, Department of Chemistry Education, 10100 Balikesir, Turkey.

1,n-Di(9-ethylcarbazol-3-yl)alkanes, where n=1-5, as the dichromophoric model compounds of poly-3-vinylcarbazoles were synthesized to examine their complexation behaviors with the electron acceptors tetracyanoethylene (TCNE) and tetranitromethane (TNM). 9,9'-Diethyl-3,3'-dicarbazolyl, di(3-ethylcarbazol-9-yl)methane, and three monomeric analogues were also included for comparison. In dichloromethane solution, the dicarbazoles formed stable 1:1 electron donor-acceptor complexes with TCNE having formation enthalpies around -3.5kcal/mol. With TNM they formed more weakly bound complexes that showed little dependence on concentration and almost zero dependence on temperature changes having nearly 0kcal/mol enthalpies of formation. The smaller gap between the two carbazole groups in 1,n-di(9-ethylcarbazol-3-yl)alkanes with nor=3.
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http://dx.doi.org/10.1016/j.saa.2008.07.034DOI Listing
January 2009

Charge-transfer complex formation between p-chloranil and 1,n-dicarbazolylalkanes.

Spectrochim Acta A Mol Biomol Spectrosc 2007 Apr 26;66(4-5):1063-7. Epub 2006 May 26.

Sakarya University, Faculty of Arts and Sciences, Department of Chemistry, 54100 Sakarya, Turkey.

Dimer model compounds of polyvinylcarbazoles (1,n-di(N-carbazolyl)alkanes, when n=1-5) were synthesized to model the effects of distance and orientation between carbazole groups in polymeric systems. Charge-transfer (CT) complexes of carbazole, N-ethylcarbazole and 1,n-di(N-carbazolyl)alkanes with p-chloranil (p-CHL) have been investigated spectrophotometrically in dichloromethane. The colored products are measured spectrophotometrically at different wavelength depending on the electronic transition between donors and acceptor. The formation constants of the CT complexes were determined by the Benesi-Hildebrand equation. The thermodynamic parameters were calculated by Van't Hoff equation. Stochiometries of the complexes formed between donors and acceptor were defined by the Job's method of the continuous variation and found in 1:1 complexation with donor and acceptor at the maximum absorption bands.
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http://dx.doi.org/10.1016/j.saa.2006.04.041DOI Listing
April 2007

Charge transfer complex formation between p-chloranil and 1,n-di(9-anthryl)alkanes.

Spectrochim Acta A Mol Biomol Spectrosc 2006 Jun 4;64(3):711-6. Epub 2006 Jan 4.

Sakarya University, Faculty of Arts and Sciences, Department of Chemistry, Sakarya, Turkey.

Dimer model compounds of polyvinylanthracenes (1,n-di(9-anthryl)alkanes, when n=1-5) were synthesized to model the effects of distance and orientation between anthracene groups in polymeric systems. Charge transfer (CT) complexes of anthracene, 9-methylanthracene and 1,n-di(9-anthryl)alkanes with p-chloranil (p-CHL) have been investigated spectrophotometrically in dichloromethane. The colored products are measured spectrophotometrically at different wavelength depending on the electronic transition between donors and acceptor. The formation constants of the CT complexes were determined by the Benesi-Hildebrand equation. The thermodynamic parameters were calculated by Van't Hoff equation. Stochiometries of the complexes formed between donors and acceptor were defined by the Job's method of the continuous variation and found in 1:1 complexation with donor and acceptor at the maximum absorption bands.
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http://dx.doi.org/10.1016/j.saa.2005.07.073DOI Listing
June 2006