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Volumn 11, Issue 2, 2005, Pages 495-508

On the electronic structure of ethidium

Author keywords

Aromatic heterocycle; Crystal structure; Intercalating agent; NMR spectroscopy; Stacking interactions

Indexed keywords

AROMATIC COMPOUNDS; CARRIER CONCENTRATION; ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; FLUORESCENCE; HYDROGEN; LIGHT ABSORPTION; NITROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 12444287913     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400559     Document Type: Article
Times cited : (59)

References (69)
  • 14
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    • b) H. W. Zimmermann, Angew. Chem. 1986, 98, 115-131; Angew. Chem. Int. Ed. Engl. 1986, 25, 115-130.
    • (1986) Angew. Chem. , vol.98 , pp. 115-131
    • Zimmermann, H.W.1
  • 15
    • 84985615449 scopus 로고
    • b) H. W. Zimmermann, Angew. Chem. 1986, 98, 115-131; Angew. Chem. Int. Ed. Engl. 1986, 25, 115-130.
    • (1986) Angew. Chem. Int. Ed. Engl. , vol.25 , pp. 115-130
  • 28
    • 12444256177 scopus 로고    scopus 로고
    • See ref. [11] for the complete experimental procedures and NMR characterization of compounds 2-10 and 13-15
    • See ref. [11] for the complete experimental procedures and NMR characterization of compounds 2-10 and 13-15.
  • 35
    • 12444278734 scopus 로고    scopus 로고
    • note
    • 13C NMR assignments reported here.
  • 36
    • 12444292516 scopus 로고    scopus 로고
    • note
    • 1H NMR assignments and δ difference maps of ethidium chloride (1), 3,8-diamino-6- phenylphenanthridine (16), 5-ethyl-6-phenylphenanthridinium chloride (11), and 6-phenylphenanthridine (17).
  • 37
    • 12444263062 scopus 로고    scopus 로고
    • PhD Thesis, University of California, San Diego
    • N. W. Luedtke, PhD Thesis, University of California, San Diego, 2003.
    • (2003)
    • Luedtke, N.W.1
  • 43
    • 12444300932 scopus 로고    scopus 로고
    • note
    • 8 may be dominated by differences in electrone-gativities of nitrogen versus hydrogen and may, therefore, not be indicative of the π-electron densities at these positions.
  • 46
    • 12444321148 scopus 로고    scopus 로고
    • note
    • 6 bond is, in fact, nearly a full double bond.
  • 47
    • 12444284795 scopus 로고    scopus 로고
    • note
    • [45]
  • 48
    • 12444261490 scopus 로고    scopus 로고
    • note
    • See Supporting Information for IR spectra of ethidium chloride (1), tetramethyl-ethidium chloride (12), and 5-ethyl-6-phenylphenanthridinium chloride (11).
  • 49
    • 0003608530 scopus 로고
    • 2nd ed., Aldrich Chemical Company Inc.
    • For the IR spectra of other aromatic iminium derivatives see: The Aldrich Library of Infrared Spectra (Ed.: C. J. Pouchert), 2nd ed., Aldrich Chemical Company Inc., 1975.
    • (1975) The Aldrich Library of Infrared Spectra
    • Pouchert, C.J.1
  • 51
    • 12444290673 scopus 로고    scopus 로고
    • note
    • Early theoretical studies claim that the 6-phenyl ring of ethidium is responsible for its lack of planarity (see ref. [26]). A survey of the Cambridge Crystallographic Database, however, suggests that electron donating groups break the planarity of aromatic systems more effectively than phenyl rings. This can be observed for the following series of phenanthrine-based compounds (twist angles indicated in parenthesis): phenanthrine (0.8), 6-napthyl-phenanthrine (0.9), 6-(N,N-dimethyl aniline)-phenanthrine (2.0).
  • 52
    • 12444288293 scopus 로고    scopus 로고
    • note
    • The atomic coordinates of the hydrogen atoms were determined using electron difference maps. See Supporting Information for the ORTEP drawing and crystallographic parameters for compounds 1-3. CCDC-247 564 (1), -247 565 (2), and -247 566 (3) contain the atomic coordinates for these structures. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ ccdc.cam.uk).
  • 53
    • 12444312727 scopus 로고    scopus 로고
    • note
    • 5.
  • 56
    • 12444291915 scopus 로고    scopus 로고
    • note
    • A linear correlation between bond-length/bond-order has already been established for the nitrogen-carbon bonds of phenanthidine-containing molecules (see ref. [42]).
  • 58
    • 12444284794 scopus 로고    scopus 로고
    • note
    • 13C chemical shifts very similar to the nitrogen-bound carbon of aniline. This supports the premise that the contributions made by N-C polarization and hybridization should not have a significant influence on the charges calculated at these positions.
  • 60
    • 12444321717 scopus 로고    scopus 로고
    • note
    • [33]
  • 61
    • 12444301536 scopus 로고    scopus 로고
    • note
    • 6. This position is expected to be electropositive (see Supporting Information and refs. [22] and [59]).
  • 69
    • 12444309112 scopus 로고    scopus 로고
    • note
    • Crystal structures of ethidium intercalated into nucleotide diphosphates (see ref. [12] for an example) are currently the only high-resolution structures of DNA-ethidium intercalation complexes available. These data provide evidence that ethidium can intercalate from both the major and minor grooves of DNA.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.