Crystal structure of N-(3,4-dichlorobenzylidene)-4-methylaniline, C14H11Cl2N

Yuan, Hua; Chen, Chunni; Wang, Linyan

doi:10.1515/ncrs-2016-0225

Cited by 1 publication

(3 citation statements)

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“…16‐29 in Table ). We thought that the heavy atom effect indicator ( D ) for halogens reported in our previous work may improve the correlation results. Thus, D (X) and D (Y) were included to build the quantitative structure‐property relationship model for ν max , but D (Y) was eliminated due to its large P ‐value ( P > 0.05).…”

Section: Resultsmentioning

confidence: 88%

“…In this paper, thirty‐seven 2,5‐disubstituted pyrimidines with various substituents (X/Y=NH 2 , CH 3 , OCH 3 , NMe 2 , CF 3 , NO 2 , Cl, Br, I) have been synthesized according to the reported methods . The structures of all these compounds have been characterized by nuclear magnetic resonance (NMR) spectra, as shown in Table .…”

Section: Experiments and Calculation Methodsmentioning

confidence: 99%

“…The excited‐state substituent constant

σ_{CC}^{ex}

is a molecular descriptor describing the stability of the excited state . It has been widely applied to the quantitative structure‐property relationship study of the ultraviolet maximum absorption, the NMR chemical shifts, and the reduction potentials . Here, we also take

σ_{CC}^{ex}

into consideration to correlate the UV absorption energy.…”

Section: Experiments and Calculation Methodsmentioning

confidence: 99%

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Substituent effects on the UV absorption energy of 2,5‐disubstituted pyrimidines

Yuan

Chen

et al. 2018

J of Physical Organic Chem

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Pyrimidine-containing molecules have been extensively investigated in organic light emitting devices (OLEDs), solar cells, liquid crystals, and so on due to their perfect photoelectric properties. Ultraviolet (UV) absorption is one of the interesting photoelectric properties. Systematical study of the substituent effects on the UV absorption energy of pyrimidine derivatives will guide to design functional molecules with specific photoelectric properties. In this paper, thirty-seven 2-X-5-Y pyrimidines with various substituents (X/Y=NH 2 , CH 3 , OCH 3 , NMe 2 , CF 3 , NO 2 , Cl, Br, I) were synthesized, and their UV spectra were recorded in anhydrous ethanol. The maximum absorption wavelength λ max (nm) were obtained and converted to wavenumber ν max (cm -1 ) (ν max = 1/λ max ) for quantitative structure-property relationship study. Hammett parameters (σ, σ F , σ R ), electronegativity (χ), the excited-state substituent effect parameter (σ ex CC ), and the heavy atom effect indicator (D) were employed as descriptors characterizing the molecular structure. By stepwise regression, a 5-descriptor linear regression model was built as ν max = 35 864.8122 + 6743.7901σ R (X) + 8587.9937σ R (Y) − 2042.7280Δσ 2 + 1106.0034D(X) + 1451.8873χ(X) (R = 0.9861, S = 693.70, ARD = 1.49%, F = 218.68, R cv = 0.9775, S cv = 881.25, ARD cv = 1.82%, n = 37). The model is proved of good stability and predictive performance by leave-one-out cross validation. Compared with the benzylideneaniline derivatives with C═N bridge group, the substituent effects on the UV absorption energy of 2,5-disubstituted pyrimidines are quite different and much more complex. KEYWORDS 2,5-disubstituted pyrimidine, quantitative structure-property relationship, substituent effect, UV absorption

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Section: Resultsmentioning

confidence: 88%

Section: Experiments and Calculation Methodsmentioning

confidence: 99%

“…The excited‐state substituent constant