Vibrational spectra of benzene derivatives—XVII. Benzonitrile and substituted benzonitriles

Green, J.H.S.; Harrison, David

doi:10.1016/0584-8539(76)80166-3

Cited by 92 publications

(46 citation statements)

References 19 publications

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“…2͑d͔͒ are listed in Table I. From Table I, it can be seen that all vibrational features of physisorbed benzonitrile agree well with the infrared analyses of liquid phase benzonitrile 22 and previous infrared studies of physisorbed benzonitrile on Au͑100͒. 23 However, the features of chemisorbed benzonitrile ͓Figs.…”

Section: A High-resolution Electron Energy Loss Spectroscopysupporting

confidence: 71%

Selective attachment of benzonitrile on Si(111)-7×7: Configuration, selectivity, and mechanism

Tao

Wang²,

Chen³

et al. 2002

Phys. Rev. B

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The cycloaddition of benzonitrile with Si͑111͒-7ϫ7 has been investigated as a model system for understanding the interaction of conjugated -electron systems with Si͑111͒-7ϫ7 using high-resolution electron energy loss spectroscopy, x-ray photoelectron spectroscopy ͑XPS͒, ultraviolet photoelectron spectroscopy, scanningtunneling microscopy ͑STM͒, and density-functional-theory calculation ͑perturbative Beck-Perdew functional in conjugation with a basis set of DN**͒. Vibrational features of chemisorbed benzonitrile unambiguously demonstrate that the cyano group directly interacts with Si surface dangling bonds, evidenced in the disappearance of CwN stretching mode around 2256 cm Ϫ1 coupled with the appearance of CvN stretching mode at 1623 cm Ϫ1 and the retention of all vibrational signatures of phenyl ring. XPS shows that both C 1s and N 1s core levels of the cyano groups display large down-shifts by 2.5 and 1.5 eV, respectively, after chemisorption. A smaller down-shift of ϳ0.8 eV is observed for the C 1s core level of phenyl group due to the weaker inductive effect of the formed CvN groups in chemisorbed benzonitrile than that of CwN groups in physisorbed molecules. Compared with physisorbed molecules, the photoemission from CN orbitals of chemisorbed benzonitrile is significantly reduced, suggesting the direct involvement of CN in the surface binding. These experimental results show that the covalent attachment of benzonitrile on Si͑111͒-7ϫ7 occurs in a selective manner through the ͑2ϩ2͒ cycloaddition between the cyano group and the adjacent adatom-rest atom pair. The cycloadduct formed contains an intact phenyl ring protruding into vacuum, retaining aromaticity. This functionalized Si surface may serve as a substrate for further modification or act as an intermediate for fabrication of multilayer organic thin films or materials syntheses in vacuum.

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Section: A High-resolution Electron Energy Loss Spectroscopysupporting

confidence: 71%

Selective attachment of benzonitrile on Si(111)-7×7: Configuration, selectivity, and mechanism

Tao

Wang²,

Chen³

et al. 2002

Phys. Rev. B

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“…In each case, the blanks were in good agreement with literature spectra [37][38][39][40][41], and with blanks run previously in this laboratory. Each blank experiment was then irradiated by the H 2 O/Pyrex-filtered output of a 200 W Hg arc lamp for 1.0 h and no changes were noted, other than in the Ar/ CrCl 2 O 2 blank, where the growth of very weak bands due to photochemical reaction with impurity H 2 O was seen [21].…”

Section: Resultsmentioning

confidence: 77%

Matrix isolation and theoretical investigation of the photochemical reaction of CrCl2O2 with benzenes substituted with electron withdrawing groups

Hoops

Ault

2007

Chemical Physics

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“…The vibrational spectra of benzene derivatives, benzonitriles and substituted benzonitriles were reported by Green and Harrison [3]. Pavan Kumar and Harrison [4] reported the vibrational analysis of substituted benzonitriles.…”

Section: Introductionmentioning

confidence: 94%

Molecular structure, vibrational spectroscopic (FT-IR, FT-Raman), UV and NBO analysis of 2-chlorobenzonitrile by density functional method

Krishnan

Saleem

Subashchandrabose

et al. 2011

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Vibrational spectra of benzene derivatives—XVII. Benzonitrile and substituted benzonitriles

Cited by 92 publications

References 19 publications

Selective attachment of benzonitrile on Si(111)-7×7: Configuration, selectivity, and mechanism

Selective attachment of benzonitrile on Si(111)-7×7: Configuration, selectivity, and mechanism

Matrix isolation and theoretical investigation of the photochemical reaction of CrCl2O2 with benzenes substituted with electron withdrawing groups

Molecular structure, vibrational spectroscopic (FT-IR, FT-Raman), UV and NBO analysis of 2-chlorobenzonitrile by density functional method

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