当前位置：
X-MOL 学术
›
J. Phys. Chem. C
›
论文详情
Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
C–H···O Hydrogen Bonding in Pentamers of Isatin
The Journal of Physical Chemistry C ( IF 3.3 ) Pub Date : 2017-09-21 00:00:00 , DOI: 10.1021/acs.jpcc.7b07444 Angela M. Silski 1 , Ryan D. Brown 1 , Jacob P. Petersen 1 , Joseph M. Coman 1 , David A. Turner 1 , Zach M. Smith 2 , Steven A. Corcelli 1 , John C. Poutsma 2 , S. Alex Kandel 1
The Journal of Physical Chemistry C ( IF 3.3 ) Pub Date : 2017-09-21 00:00:00 , DOI: 10.1021/acs.jpcc.7b07444 Angela M. Silski 1 , Ryan D. Brown 1 , Jacob P. Petersen 1 , Joseph M. Coman 1 , David A. Turner 1 , Zach M. Smith 2 , Steven A. Corcelli 1 , John C. Poutsma 2 , S. Alex Kandel 1
Affiliation
|
Self-assembled monolayers of 1H-indole-2,3-dione (isatin), 3-methyl 2-oxindole, and 7-fluoroisatin are observed on the Au(111) surface via scanning tunneling microscopy (STM). We observed that isatin forms pentamers with density functional theory providing support for a cyclic structure stabilized by both N–H···O and C–H···O hydrogen bonds between neighboring molecules. The C–H···O bond is made between the 7-position C–H acting as the hydrogen bond donor and the 3-position carbonyl as the hydrogen bond acceptor, and calculations show that the isatin pentamer structure is 12 kJ/mol more stable than the dimer. When the 3-position carbonyl is removed and replaced with a methyl group (3-methyl 2-oxindole), we observe a monolayer with a mixture of catemer chains and pentameric clusters that are qualitatively different from those of isatin. Pentamer formation is completely broken when the 7-position hydrogen is removed and replaced with fluorine; the monolayer of 7-fluoroisatin is composed of a mixture of close packed ordered domains and hexamer clusters. The role of C–H···O bonding in forming isatin pentamers is supported by electrospray ionization mass spectrometry measurements, which show a propensity for isatin cluster formation, including magic-number isatin pentamers, while 3-methyl 2-oxindole and 7-fluoroisatin show relatively little clustering under the same conditions.
中文翻译：
Isatin五聚体中的C–H···O氢键
1 H的自组装单层通过扫描隧道显微镜（STM）在Au（111）表面观察到了2-吲哚-2,3-二酮（靛红），3-甲基2-羟吲哚和7-氟靛红。我们用密度泛函理论观察到，靛红形成五聚体，为由相邻分子之间的N–H··O和C–H···O氢键稳定的环状结构提供了支持。C–H···O键是在充当氢键供体的7位C–H和作为氢键受体的3位羰基之间建立的，计算表明，靛红五聚体结构为12 kJ / mol比二聚体更稳定。当3位羰基被除去并被甲基（3-甲基2-羟吲哚）取代时，我们观察到单层的质子交换链和五聚体簇的混合物在质量上不同于伊斯丁。当除去7位氢并用氟代替时，五聚体的形成被完全破坏。7-氟异丁香素的单层由紧密堆积的有序结构域和六聚体簇的混合物组成。C–H···O键在形成Isatin五聚体中的作用得到了电喷雾电离质谱测量的支持，这表明形成Isatin簇的倾向，包括幻数Isatin五聚体，而3-甲基2-羟吲哚和7-在相同条件下，氟异丁香素显示出相对较少的聚集。
更新日期：2017-09-21
中文翻译：
Isatin五聚体中的C–H···O氢键
1 H的自组装单层通过扫描隧道显微镜（STM）在Au（111）表面观察到了2-吲哚-2,3-二酮（靛红），3-甲基2-羟吲哚和7-氟靛红。我们用密度泛函理论观察到，靛红形成五聚体，为由相邻分子之间的N–H··O和C–H···O氢键稳定的环状结构提供了支持。C–H···O键是在充当氢键供体的7位C–H和作为氢键受体的3位羰基之间建立的，计算表明，靛红五聚体结构为12 kJ / mol比二聚体更稳定。当3位羰基被除去并被甲基（3-甲基2-羟吲哚）取代时，我们观察到单层的质子交换链和五聚体簇的混合物在质量上不同于伊斯丁。当除去7位氢并用氟代替时，五聚体的形成被完全破坏。7-氟异丁香素的单层由紧密堆积的有序结构域和六聚体簇的混合物组成。C–H···O键在形成Isatin五聚体中的作用得到了电喷雾电离质谱测量的支持，这表明形成Isatin簇的倾向，包括幻数Isatin五聚体，而3-甲基2-羟吲哚和7-在相同条件下，氟异丁香素显示出相对较少的聚集。
京公网安备 11010802027423号