Photoelectron Spektra of Azabenzenes and Azanaphthalenes: II. A Reinvestigation of Azanaphthalenes by High‐Resolution Photoelectron Spectroscopy

Brogli, Franz; Heilbronner, E.; Kobayashi, Tsunetoshi

doi:10.1002/hlca.19720550131

Cited by 99 publications

(43 citation statements)

References 22 publications

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“…In the next paper of this series [14] we show that for azabenzenes and azanaphthalenes the n-orbital energies -Iv, J(calc. ), calculated according to a simple HMO-procedure, correlate closely with the vertical ionization potentials Iv, J of the corresponding PE.…”

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confidence: 82%

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Photoelectron Spectra of Azabenzenes and Azanaphthalenes: I. Pyridine, diazines, s‐triazine and s‐tetrazine

Gleiter

Heilbronner

Hornung

1972

Helvetica Chimica Acta

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202

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The experimental and theoretical basis of a recently proposed reassignment of the bands in the PE. spectra of pyridine, pyridazine, pyrimidine and pyrazine is discussed in detail. A characteristic feature of the derived orbital sequence is that it takes the ‘through‐space’ and ‘through‐bond’ interaction between the ‘lone pair’ basis orbitals explicitly into account. A simple parametrization of the orbital energies, based on HMO‐type models for the π‐orbitals and for the ‘lone pair’ linear combinations, yields excellent agreement with the observed band positions in the PE. spectra of s‐triazine and s‐tetrazine. Our new assignment is compared to those proposed previously.

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Section: )mentioning

confidence: 82%

“…spectra of benzene [ l l ] [15], naphthalene [14] [16], or other hydrocarbons containing larger n-electron systems [16] [17], removal of an electron from one of their two highest occupied n-orbitals leads to PE. bands of type 1.…”

Section: )mentioning

confidence: 99%

Photoelectron Spectra of Azabenzenes and Azanaphthalenes: I. Pyridine, diazines, s‐triazine and s‐tetrazine

Gleiter

Heilbronner

Hornung

1972

Helvetica Chimica Acta

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202

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“…In these cases, we consider the average value (see Table 3). For fluorene [38], (b) [39], (c) [40], (d) [41], (e) [42], (f) [43], (g) [44], (h) [45], (k) [46], (j) [47], (i) [48], (l) [49], (m) [50], (n) [51], (o) [52], (p) [53], (q) [54], (r) [55], (s) [56], (t) [57], (u) [58], (v) [59], (w) [60], (x) [61]. (14) and naphthalene (18) measurements of the vertical EAs are available.…”

Section: Resultsmentioning

confidence: 99%

Rapid quantitative prediction of ionization energies and electron affinities of polycyclic aromatic hydrocarbons

Modelli

Mussoni

2007

Chemical Physics

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“…The importance of this effect is obvious from photoelectron spectroscopic data (cf. [24] and Section 3) which suggest that an inductive perturbation Sax at the heteroatom induces a perturbation of m . Sax (m 1/3) a t the adjacent carbon atoms.…”

Section: Syntheses Ground State Properties Arzd Analyses Oj N M R mentioning

confidence: 94%

Electronic Structure and Photophysical Properties of Isoindole and its Benzo[f]‐ and Dibenzo[e,g]‐Derivatives

Rettig

Wirz

1976

Helvetica Chimica Acta

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Suwvnavy. The synthesis of N-methyl-benz[f]isoindole (2) and N-methyl-dibenz[e, glisoindole (3) is reported. The NMR. spectra of N-methyl-isoindole (1) and of 2 have been analysed and the implications concerning the alternation of bond lengths are discussed. The photophysical properties of 1 to 3 have been investigated by the following methods: He1 photoelectron (PE.) spcctroscopy, UV./VIS. absorption (polarization measurements by the stretched-foil technique) and emission spectroscopy (fluorescence spectra, lifetimes and quantum yields, phosphorescence spectra), and flash spectroscopy (triplet-triplet absorption spectra). The discussion of the results is based on HMO. and PPP SCF CI. calculations and points to the relationship between the heterocydes 1 to 3 and the corresponding benzenoid hydrocarbons obtained by rcplacenient of the -Nl\le-subunit by -CH=CH-. Some comments concerning the ground state properties of isoindole and related compounds are derived from the analysis of their electronic structure.In the resonance theory formalism isoindole is represented by a single unexcited, o-quinonoid structure only. Indeed, the parent system is a highly reactive compound which has until recently [2] resisted many attempts to its isolation. The chemistry of isoindoles with a free NH group is complicated by a tautomeric equilibrium with the isoindolenine form and subsequent polymerization [Za]. Hence, alkylation of the nitrogen atom greatly increases the stability of isointloles. N-Methyl-isoindole (1) is stable at room temperature in the absence of acid and oxygen and has been synthesized as the first representative of this heterocycle in 1951 by Wittig et al. [3]. Since then, numerous studies concerned with the synthesis and reactivity of isoindole and its derivatives have been reported [4] and several theoretical papers have dealt with the question of its 'aromaticity ' [5]. No investigation of the photophysical or photochemical properties of this interesting chromophore has appeared to date, apart from some rather divergent results of semiempirical SCF CX. calculations [5f] [5i] [6] and more recently the UV. spectrum of isoindole [Za] and some of its derivatives 171. We have chosen 1 as the parent substrate of the present study because it is readily synthesized [S] and purified. The N-methyl substituent may be considered as a minor perturbation to the electronic structure of the z-system which does not effectively reduce the symmetry. The introduction of the methyl blocking-group has further made possible the isolation and investigation of the benzo[f]homologue 2, prior 1) 2)Taken in part from the Ph. D. thesis of W. R. [l].

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Photoelectron Spektra of Azabenzenes and Azanaphthalenes: II. A Reinvestigation of Azanaphthalenes by High‐Resolution Photoelectron Spectroscopy

Abstract: Summary. The bands with I, < 13 eV in the photoclcctron spsctra of quinoline (IX), isoquinoline (X), cinnoline (XI), quinazoline (XII), and quinoxaline (XIII) h a w been reassigned in a way consistent with the assignment proposed for pyridine (11). the diazines (

Cited by 99 publications

References 22 publications

Photoelectron Spectra of Azabenzenes and Azanaphthalenes: I. Pyridine, diazines, s‐triazine and s‐tetrazine

Photoelectron Spectra of Azabenzenes and Azanaphthalenes: I. Pyridine, diazines, s‐triazine and s‐tetrazine

Rapid quantitative prediction of ionization energies and electron affinities of polycyclic aromatic hydrocarbons

Electronic Structure and Photophysical Properties of Isoindole and its Benzo[f]‐ and Dibenzo[e,g]‐Derivatives

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