1-(5-Carboxypentyl)-2,3,3-trimethyl-3 H -indol-1-ium bromide monohydrate

Winstead, Angela; Hart, Krystal; Hijji, Yousef M.; Jasinski, Jerry P.; Butcher, Ray J.

doi:10.1107/s1600536809049204

1-(5-Carboxypentyl)-2,3,3-trimethyl-3 H -indol-1-ium bromide monohydrate

Journal Article · Wed Dec 16 00:00:00 EST 2009 · Acta Crystallographica. Section E

DOI:https://doi.org/10.1107/s1600536809049204· OSTI ID:1625737

Winstead, Angela ^[1]; Hart, Krystal ^[2]; Hijji, Yousef M. ^[2]; Jasinski, Jerry P. ^[3]; Butcher, Ray J. ^[4]

Morgan State Univ., Baltimore, MD (United States). Dept. of Chemistry; DOE/OSTI
Morgan State Univ., Baltimore, MD (United States). Dept. of Chemistry
Keene State College, Keene, NH (United States). Dept. of Chemistry
Howard Univ., Washington, DC (United States). Dept. of Chemistry

In the title compound, C17H24NO2 + BrH2O, the pentyl group chain in the cation extends nearly perpendicular [N— C—C—C = 64.4 (3)°] to the mean plane of the indole ring with the carboxyl end group twisted such that the dihedral angle between the mean planes of the indole and carboxy groups measures 43.2 (4)°. Both ions in the salt form intermolecular hydrogen bonds (O—HBr and O—HO) with the water molecule. As a result of the BrH—O— HBr interactions, a zigzag chain is formed in the c-axis direction. The crystal packing is influenced by the collective action of the O—HO and O—HBr intermolecular interactions as well as – stacking intermolecular interactions between adjacent benzyl rings of the indole group [centroid–centroid distance = 3.721 (13) Å ] and intermolecular C—H interactions between a methyl hydrogen and the benzyl ring of the indole group. The O—HBr interactions form a distorted tetrahedral array about the central Br atom. A MOPAC AM1 calculation provides support to these observations.

Research Organization:: Morgan State Univ., Baltimore, MD (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: FG02-03ER63580

OSTI ID:: 1625737

Journal Information:: Acta Crystallographica. Section E, Journal Name: Acta Crystallographica. Section E Journal Issue: 1 Vol. 66; ISSN 1600-5368; ISSN ACSEBH

Publisher:: International Union of CrystallographyCopyright Statement

Country of Publication:: United States

Language:: English

References (11)

TOTO and YOYO: New very bright fluorochromes for DNA content analyses by flow cytometry Hirons, G. T.; Fawcett, J. J.; Crissman, H. A. Cytometry, Vol. 15, Issue 2 https://doi.org/10.1002/cyto.990150206	journal	February 1994
Isolation and Quality Control of Functional Mitochondria Hartwig, Sonja; Kotzka, Jorg; Lehr, Stefan Methods in Molecular Biology https://doi.org/10.1007/978-1-0716-1266-8_3	book	January 2021
Practical syntheses of dyes for difference gel electrophoresis Jung, Michael E.; Kim, Wan-Joong Bioorganic & Medicinal Chemistry, Vol. 14, Issue 1 https://doi.org/10.1016/j.bmc.2005.07.068	journal	January 2006
Capillary electrophoresis with laser-induced fluorescence detection of PCR fragments using thiazole orange Schwartz, Herbert E.; Ulfelder, Kathi J. Analytical Chemistry, Vol. 64, Issue 15 https://doi.org/10.1021/ac00039a019	journal	August 1992
High-Sensitivity Capillary Electrophoresis of Double-Stranded DNA Fragments Using Monomeric and Dimeric Fluorescent Intercalating Dyes Zhu, Huiping.; Clark, Steven M.; Benson, Scott C. Analytical Chemistry, Vol. 66, Issue 13 https://doi.org/10.1021/ac00085a004	journal	July 1994
J-aggregate formation of a carbocyanine as a quantitative fluorescent indicator of membrane potential Reers, Martin; Smith, Thomas W.; Chen, Lan Bo Biochemistry, Vol. 30, Issue 18 https://doi.org/10.1021/bi00232a015	journal	May 1991
Phase transition and dye aggregation in phospholipid-amphiphilic dye liposome bilayers Kurihara, Kazue; Toyoshima, Yoshinori; Sukigara, Mitsunori The Journal of Physical Chemistry, Vol. 81, Issue 19 https://doi.org/10.1021/j100534a009	journal	September 1977
Vectorial photoinduced electron transfer between phospholipid membrane-bound donors and acceptors Armitage, Bruce; O'Brien, David F. Journal of the American Chemical Society, Vol. 114, Issue 19 https://doi.org/10.1021/ja00045a009	journal	September 1992
Conjugating a Cyanine Dye to a Polymer Surface. In Search of a Monomeric Dye in Apolar Media Pertusati, Fabrizio; Menger, Fredric M. The Journal of Organic Chemistry, Vol. 73, Issue 7 https://doi.org/10.1021/jo7027294	journal	April 2008
A new minor groove binding asymmetric cyanine reporter dye for real-time PCR Bengtsson, M. Nucleic Acids Research, Vol. 31, Issue 8 https://doi.org/10.1093/nar/gng045	journal	April 2003
A short history of SHELX Sheldrick, George M. Acta Crystallographica Section A Foundations of Crystallography, Vol. 64, Issue 1, p. 112-122 https://doi.org/10.1107/S0108767307043930	journal	December 2007

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