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7 references were found for 3 of 3 substances in CAPLUS and MEDLINE

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CAPLUS: Copyright © 2007 American Chemical Society. All Rights Reserved. (The UK patent
material in this product/service is UK Crown copyright and is
made available with permission. © Crown Copyright. The French
(FR) patent material in this product/service is made available
from Institut National de la Propriete Industrielle (INPI).)
MEDLINE: Produced by the U.S. National Library of Medicine
REGISTRY: Copyright © 2007 American Chemical Society. All Rights Reserved. (Some records
contain information from GenBank(R). See also: Benson D.A.,
Karsch-Mizrachi I., Lipman D.J., Ostell J., Rapp B.A., Wheeler D.L.
Genbank. Nucl. Acids Res. 28(1):15-18 (2000). Property values
tagged with IC are from the ZIC/VINITI data file provided by
InfoChem.)
CASREACT: Copyright © 2007 American Chemical Society. All Rights Reserved. (In addition to
reactions indexed by CAS, CASREACT contains reactions derived
from the following sources: ZIC/VINITI database (1974-1999)
provided by InfoChem, INPI data prior to 1986, and
Biotransformations database compiled under the direction of
Professor Dr. Klaus Kieslich.)
CHEMLIST, CHEMCATS: Copyright © 2007 American Chemical Society. All Rights Reserved.

Bibliographic Information

Description of Carbo-oxocarbons and Assessment of Exchange-Correlation Functionals

for the DFT Description of Carbo-mers. Lepetit, Christine; Chermette, Henry; Gicquel,
Mickaeel; Heully, Jean-Louis; Chauvin, Remi. Laboratoire de Chimie de Coordination, UPR 8241,
CNRS, Toulouse, Fr. Journal of Physical Chemistry A (2007), 111(1), 136-149. Publisher:
American Chemical Society, CODEN: JPCAFH ISSN: 1089-5639. Journal written in English. CAN
146:142120 AN 2006:1303136 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R))
Abstract

Mono- and polycyclic valence isomers of carbo-[3]oxocarbon C9O3 and carbo-[5]oxocarbon C15O5
have been characterized on the singlet spin state potential energy surface. By contrast to their
geometry, their relative stability is highly sensitive to the calcn. level. The performance of LDA,
GGA, meta-GGA, and hybrid functionals is compared to that of HF, post-HF, and
multiconfigurational calcns. The results obtained for C9O3 are compared to those obtained for
hydrocarbon analogs such as [3]pericyclyne C9(H2)3 and carbo-[3]radialene C9(CH2)3 and are
analyzed on the basis of an energy decompn. scheme. The resp. role of the exchange and
correlation counterparts of the functional in the discrepancy of the results is discussed.

Bibliographic Information

Computational Studies of Ethynyl- and Diethynyl-Expanded Tetrahedranes, Prismanes,

Cubanes, and Adamantanes. Bachrach, Steven M.; Demoin, Dustin W. Department of
Chemistry, Trinity University, San Antonio, TX, USA. Journal of Organic Chemistry (2006),
71(14), 5105-5116. Publisher: American Chemical Society, CODEN: JOCEAH ISSN: 0022-3263.
Journal written in English. CAN 145:145047 AN 2006:536730 CAPLUS (Copyright (C) 2007
ACS on SciFinder (R))

Abstract

B3LYP/6-31+G(d) and MP2/6-31+G(d) computations were performed on a series of ethynyl- and

diethynyl-expanded tetrahedranes, prismanes, cubanes and adamantanes. Every ethynyl
expansion reduces the ring strain energy of the cage. The deprotonation energies of the cage
poly-ynes are exceptionally low; we est. that the gas-phase deprotonation energy of the diethynyl-
expanded cubane is about 309 kcal mol-1. The ring and cage poly-ynes can serve as effective
hosts of either lithium or sodium cation, where the best host maximizes the no. of interactions of
alkynyl groups with the cation at an ideal distance. Last, the vertical excitation energies of the
poly-ynes and their conjugate bases suggest that the alkynyl groups are interacting through
space. The poly-ynes express a broad range of absorption energies, indicating that these mols.
are potential targets in expressly designed optical applications.

Bibliographic Information

ELF Analysis of Out-of-Plane Aromaticity and In-Plane Homoaromaticity in

Carbo[N]annulenes and [N]Pericyclynes. Lepetit, C.; Silvi, B.; Chauvin, R. Laboratoire de
Chimie de Coordination, UPR 8241 CNRS, Toulouse, Fr. Journal of Physical Chemistry A (2003),
107(4), 464-473. Publisher: American Chemical Society, CODEN: JPCAFH ISSN: 1089-5639.
Journal written in English. CAN 138:187242 AN 2003:8384 CAPLUS (Copyright (C) 2007 ACS
on SciFinder (R))

Abstract

The aromaticity and homoaromaticity in ring carbomers of [N]annulenes and [N]cycloalkanes (i.e.,
[N]pericyclynes) are investigated using the topol. anal. of the electron localization function (ELF).
In a qual. viewpoint, the ELF picture of aromaticity in carbo[N]annulenes is systematically
"expanded" with respect to those of the parent [N]annulenes. The ELF anal. allows us to evaluate
the wt. of the various resonance forms of carbo[N]annulenes corresponding to (i) out-of-plane
cyclic π electron delocalization and (ii) in-plane cyclic π electron homodelocalization. The latter
is also quantified for the parent [N]pericyclynes. The chem. relevance of this evaluation is
discussed by comparison with Bader's atoms-in-mols. topol. anal. of the electron d. and Huckel
anal. New criteria of homoaromaticity based on ELF anal. are proposed and further illustrated on
the archetypes of homoaromaticity such as the homotropenylium cation and the
cyclopropylcarbinyl cation.

Bibliographic Information
 Mobius aromatics arising from a C:C:C ring component. Martin-Santamaria, Sonsoles;
Lavan, Balasundaram; Rzepa, Henry S. Dep. Chem., Imperial College of Science, Technology and
Medicine, London, UK. Chemical Communications (Cambridge) (2000), (12), 1089-1090.
Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in
English. CAN 133:176855 AN 2000:380882 CAPLUS (Copyright (C) 2007 ACS on SciFinder
(R))

Abstract

Replacement of one planar C:C unit in Hueckel 4n + 2 arom. rings by a twisted C:C:C results in
chiral 4n π Mobius arom. rings.

Bibliographic Information

Cyclynes. Part 5. Pericyclynes: "exploded cycloalkanes" with unusual orbital

interactions and conformational properties. MM2 and STO-3G calculations, x-ray
crystal structures, photoelectron spectra, and electron transmission spectra. Houk, K.
N.; Scott, Lawrence T.; Rondan, Nelson G.; Spellmeyer, David C.; Reinhardt, Gerd; Hyun, James L.;
DeCicco, Gary J.; Weiss, Robert; Chen, Marie H. M.; et al. Dep. Chem., Univ. Pittsburgh,
Pittsburgh, PA, USA. Journal of the American Chemical Society (1985), 107(23), 6556-62.
CODEN: JACSAT ISSN: 0002-7863. Journal written in English. CAN 103:177919 AN
1985:577919 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R))

Abstract

Geometries and electronic structures of [N]pericyclynes, (C.tplbond.CCH2)N (I; N = 2-6), and some
permethylated analogs are examd. using Allinger's MM2 force-field and ab initio STO-3G calcns.,
photoelectron spectrscopy, and electron transmission spectroscopy. The small-ring I (N = 3, 4) are
planar, with all the angle strain absorbed by the relatively deformable acetylenic linkages. The
common-ring I (N = 5, 6) behave conformationally like cyclopentane or cyclohexane in which all
torsional interactions are eliminated. I (N = 6) has chair, twist-boat, and boat forms of essentially
identical energy. Both through-space and through-bond interactions between the acetylenic units
are important, with the former dominating in the in-plane orbitals and the latter in the out-of-plane
orbitals. The structure of decamethyl[5]pericyclyne predicted by MM2 agrees with the crystallog.
structure. The crystal structure of a tetrayne, 5,5,6,6,11,11,12,12-octamethyl-1,3,7,9-
cyclododecatetrayne, obtained in the attempted prepn. of a [4]pericyclyne, is also reported.

Bibliographic Information

(3)-, (4)-, and (5)-Pericyclyne: through-bond versus through-space interactions.

Dewar, M. J. S.; Holloway, M. K. Dep. Chem., Univ. Texas, Austin, TX, USA. Avail. NTIS.
Report (1984), (AFOSR-TR-85-0031; Order No. AD-A150608/8/GAR), 6 pp. From: Gov. Rep.
Announce. Index (U. S.) 1985, 85(10), 78. Report written in English. CAN 103:141075 AN
1985:541075 CAPLUS (Copyright (C) 2007 ACS on SciFinder (R))

Abstract

MNDO calcns. for the title pericyclynes indicate that interactions between triple bonds are
hyperconjugative in the π system and homoconjugative in the σ system, and that 3-pericyclyne
may interconvert with a valence tautomer, tricyclopropabenzene.

Bibliographic Information

[3]-, [4]-, and [5]-pericyclyne: through-bond vs. through-space interactions. Dewar,

Michael J. S.; Holloway, Mary K. Dep. Chem., Univ. Texas, Austin, TX, USA. Journal of the
Chemical Society, Chemical Communications (1984), (17), 1188-91. CODEN: JCCCAT ISSN:
0022-4936. Journal written in English. CAN 102:131261 AN 1985:131261 CAPLUS
(Copyright (C) 2007 ACS on SciFinder (R))

Abstract

MO calcns. for [3]-, [4]-, and [5]-pericyclyne showed that interaction between triple bonds are
hyperconjugative in the π -system and homoconjugative in the σ system. [3]-Pericyclyne can be
interconverted with the valence tautomer, tricyclopropabenzene.