Substituent constants (σp−) of the rotated nitro group
The geometries of a series of nine 4-substituted nitrophenols and 4-substituted nitrophenolates (X = H, CONH2, CHO, COOH, COCH3, COCl, CN, NO2, NO) and of their conformers, where the nitro group rotates by 10º from φ = 0° to φ = 90°, were optimized at the B3LYP/6-311+G** DFT level. These data were u...
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| Matična publikacija: |
Croatica chemica acta 82 (2009), 1 ; str. 139-147 |
| Glavni autor: | Dobrowolski, Michal A. (-) |
| Ostali autori: | Krygowski, Tadeusz M. (-), Cyranski, Michal K. |
| Vrsta građe: | Članak |
| Jezik: | eng |
| Predmet: | |
| Online pristup: |
Croatica Chemica Acta |
| LEADER | 02276caa a2200313 ir4500 | ||
|---|---|---|---|
| 001 | NSK01000733050 | ||
| 003 | HR-ZaNSK | ||
| 005 | 20131203105549.0 | ||
| 007 | ta | ||
| 008 | 100413s2009 ci ||| ||eng | ||
| 035 | |9 (HR-ZaNSK)735668 | ||
| 035 | |a (HR-ZaNSK)000733050 | ||
| 040 | |a HR-ZaNSK |b hrv |c HR-ZaNSK |e ppiak | ||
| 041 | 0 | |a eng |b hrv | |
| 042 | |a croatica | ||
| 080 | |a 54 |2 MRF 1998. | ||
| 100 | 1 | |a Dobrowolski, Michal A. | |
| 245 | 1 | 0 | |a Substituent constants (σp−) of the rotated nitro group : |b the interplay between the substituent effect of a rotated −NO2 group and H-bonds affecting π-electron delocalization in 4-nitrophenol and 4-Nitrophenolate complexes : a B3LYP/6-311+G** study / |c Michal A. Dobrowolski, Tadeusz M. Krygowski, Michał K. Cyranski. |
| 300 | |b Ilustr. | ||
| 504 | |a Bibliografija: 40 jed. | ||
| 504 | |a Sažetak | ||
| 520 | 8 | |a The geometries of a series of nine 4-substituted nitrophenols and 4-substituted nitrophenolates (X = H, CONH2, CHO, COOH, COCH3, COCl, CN, NO2, NO) and of their conformers, where the nitro group rotates by 10º from φ = 0° to φ = 90°, were optimized at the B3LYP/6-311+G** DFT level. These data were used to analyse the effect of rotating of the nitro group on π-electron delocalization in the ring. It has been shown that the substituent effect stabilization energy (SESE) estimated for p-substituted phenolates correlates very well with σp− constants. Based on this dependence the σp− constants for the nitro group as a function of the out-of-plane dihedral angle φ were obtained. Application of the model simulating varying strength of H-bond by approaching F− (HF) group to OH (O−) group of the 4-nitrophenol (4-nitrophenolate) with the rotating nitro group allowed to show interrelation between changes in aromaticity of the ring due to both rotation of the nitro group and changes in the strength of H-bonding. | |
| 653 | 0 | |a Stabilizacijska energija |a Aromatičnost |a Nitrofenoli |a Vodikova veza | |
| 700 | 1 | |a Krygowski, Tadeusz M. | |
| 700 | 1 | |a Cyranski, Michal K. | |
| 773 | 0 | |t Croatica chemica acta |x 0011-1643 |g 82 (2009), 1 ; str. 139-147 |w nsk.(HR-ZaNSK)000001621 | |
| 981 | |b B01/09 |p CRO | ||
| 998 | |a rado100413 |c vol2o130424 | ||
| 856 | 4 | 2 | |u http://hrcak.srce.hr/cca |y Croatica Chemica Acta |