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G. g. 0. Table 9. v. 0) AU determinations were made in κ-hexane. r. v. 1]octa-3,6-diene system. r. v. ) to this rather drastic progression in heteroatom electronegativity. Brief scrutiny of the situation reveals a possible reason for this otherwise puzzling discrepancy. v. data are reflective of the importance of two opposing operational factors contributing to the system's development of a heterohomoconjugated frame (i) lone-pair availability and (ii) energy matching between non-bonded units. e.

E. 109 to 105 and 110 to 102. In fact, the chemical shifts displayed by the β protons of each of the four systems as well as those of carbamates 108 and 103 (not given here) may be shown to yield good linear correlation when plotted against the corresponding σ~ substituent constants. r. and irrespective of heteroatom-electronegativity, the ethylene function bound to nitrogen appears not to 'sense' the presence of the remote double bond. Interestingly, a fundamentally different picture emerges when one focuses attention on the protons of the remote double bond.

Table 3. r. chemical shifts and coupling constants of the 'inner' a hydrogen of the ctctctaza[13]annulenes No. 5 __ — CDC1Û3 CDCI3 CDCI3 acetone-dj? 17 — Specti•urn was recorded at ca. 35°. Spectrum was recorded at ca. 0°. Specti■um was recorded at ca. v. spectral characteristics. As seen from the data collected in Table 4 each member is characterized by two major bands above ca. 250 nm of which the lower-energy one is invariably the weaker. Comparison of the relative energies of those bands as a function of effective heteroatom electronegativity, reveals an interesting if somewhat puzzling characteristic, namely that it is the higher energy band which appears to best reflect the change of the annulene periphery from strictly localized to extensively delocalized.

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