Experimental NMR and DFT Studies of Persistent Carbocations Derived from Hetero-Polycyclic Aromatic Hydrocarbons Containing Oxygen Atom: Dibenzob,dfuran, Benzobnaphtho1,2-dfuran, Benzobnaphtho 2,3-dfuran, Benzobnaphtho 2,1-dfuran, and Dinaphtho2,1-b:1 ',2 '-dfuran

Okazaki Takao; Nakagawa Madoka; Kitagawa ToshikazuLaali Kenneth K.

首页> 外文期刊>Bulletin of the Chemical Society of Japan >Experimental NMR and DFT Studies of Persistent Carbocations Derived from Hetero-Polycyclic Aromatic Hydrocarbons Containing Oxygen Atom: Dibenzob,dfuran, Benzobnaphtho1,2-dfuran, Benzobnaphtho 2,3-dfuran, Benzobnaphtho 2,1-dfuran, and Dinaphtho2,1-b:1 ',2 '-dfuran

【24h】

Experimental NMR and DFT Studies of Persistent Carbocations Derived from Hetero-Polycyclic Aromatic Hydrocarbons Containing Oxygen Atom: Dibenzob,dfuran, Benzobnaphtho1,2-dfuran, Benzobnaphtho 2,3-dfuran, Benzobnaphtho 2,1-dfuran, and Dinaphtho2,1-b:1 ',2 '-dfuran

机译：含氧原子杂多环芳烃衍生持久性碳正离子的实验性 NMR 和 DFT 研究：二苯并b，d呋喃、苯并b萘并1,2-d呋喃、苯并b萘并2,3-d呋喃、苯并b萘并2,1-d呋喃和二萘并2,1-b：1 '，2'-d呋喃

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

Persistent protonation carbocations generated from hetero-PAHs containing oxygen atoms in their aromatic rings, dibenzob,dfuran (5), benzobnaphtho1,2-dfuran (6), benzobnaphtho2,3-dfuran (7), benzobnaphtho2,1-dfuran (8), and dinaphtho2,1-b:1',2'-dfuran (9), were directly observed by NMR measurements in superacid. Compound 5 was protonated mainly at C(2) in FSO3H-SbF5 (1:1) or (4:1)/SO2ClF, and 6, 8, and 9 were protonated exclusively at C(5) in CF3SO3H or FSO3H/SO2ClF, whereas 7 was protonated at C(6) and C(11) to give two species in FSO3H/SO2ClF. Surprisingly, compound 5 resists protonation in FSO3H/SO2ClF to show NMR spectra corresponding to that of the intact material. Positive charge delocalization mapping for carbocations based on experimental Delta delta C-13 values indicates limited delocalization in these systems. The chemical shifts and charge delocalization modes derived by DFT calculations agreed with the experimental results.

机译：在超强酸中，通过核磁共振测量直接观察到芳香环中含有氧原子的异多环芳烃二苯并[b，d]呋喃（5）、苯并[b]萘并[1,2-d]呋喃（6）、苯并[b]萘并[2,3-d]呋喃（7）、苯并[b]萘并[2,1-d]呋喃（8）和二萘并[2,1-b：1'，2'-d]呋喃（9）。化合物 5 在 FSO3H-SbF5 （1：1）或（4：1）/SO2ClF 中主要在 C（2）处质子化，在 CF3SO3H 或 FSO3H/SO2ClF 中，化合物 6、8 和 9 仅在 C（5）处质子化，而化合物 7 在 C（6）和 C（11）处质子化，在 FSO3H/SO2ClF 中产生两种物质。令人惊讶的是，化合物 5 在 FSO3H/SO2ClF 中抵抗质子化，以显示与完整材料相对应的 NMR 波谱。基于实验 Delta delta C-13 值的碳正电荷离域映射表明这些系统中的离域有限。DFT计算得出的化学位移和电荷离域模式与实验结果一致。

著录项

来源
《Bulletin of the Chemical Society of Japan》 |2014年第11期|1235-1244|共10页
作者
Okazaki Takao; Nakagawa Madoka; Kitagawa ToshikazuLaali Kenneth K.;
展开▼
作者单位

Mie Univ, Grad Sch Engn, Dept Chem Mat, Tsu, Mie 5148507, Japan;

Univ N Florida, Dept Chem, Jacksonville, FL 32224 USA;

展开▼
收录信息
原文格式 PDF
正文语种英语
中图分类化学;
关键词

相似文献

外文文献
中文文献
专利

1. Experimental NMR and DFT Studies of Persistent Carbocations Derived from Hetero-Polycyclic Aromatic Hydrocarbons Containing Oxygen Atom: Dibenzo[b,d]furan, Benzo[b]naphtho[1,2-d]furan, Benzo[b]naphtho [2,3-d]furan, Benzo[b]naphtho [2,1-d]furan, and Dinaphtho[2,1-b:1 ',2 '-d]furan [J] . Okazaki Takao, Nakagawa Madoka, Kitagawa Toshikazu, Bulletin of the Chemical Society of Japan . 2014,第11期

机译：实验性NMR和DFT研究源自含有氧原子的杂多环芳烃烃：Dibenzo [B，D] Furan，Benzo [B]呋喃，苯并[B]萘[2,3 -D]呋喃，苯并[B]萘[2,1-D]呋喃，Dinaphtho [2,1-B：1'，2'd]呋喃
2. ChemInform Abstract: Convenient Synthesis and Dichroic Properties of Heterocyclic Quinone Dyes, 3‐(Dialkylamino)benzo(b)naphtho(2,3‐d)furan‐6,11‐diones. [J] . K. YOSHIDA, T. ADACHI, N. OGAY. KUBO Chem Inform . 1992,第4期

机译：ChemInform Abstract: Convenient Synthesis and Dichroic Properties of Heterocyclic Quinone Dyes, 3‐(Dialkylamino)benzo(b)naphtho(2,3‐d)furan‐6,11‐diones.
3. ChemInform Abstract: The Generation of Anthra(2,3‐c)furan (X) via Aromatic‐Ring Homologation of Naphtho(2,3‐c)furan. [J] . N. P. W. TU, J. C. YIP, P. W. DIBBLE Chem Inform . 1996,第25期

机译：ChemInform Abstract: The Generation of Anthra(2,3‐c)furan (X) via Aromatic‐Ring Homologation of Naphtho(2,3‐c)furan.
4. Crystal structure analysis of 4-(3'-hydroxy-2', 3'-dihydro-benzobfuran-2-yl)-7-methylcoumarin [C] . Naresh Sharma National Conference on Recent Advances in Experimental and Theoretical Physics . 2018

机译：4-（3'-Hydroxy-2'，3'-二氢-Benzo B Furan-2-Y1）-7-甲基伞林的晶体结构分析
5. 5-(4-Fluorophenyl)-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran [O] . Hong Dae Choi, Pil Ja Seo, Uk Lee 2014

机译：5-(4-Fluorophenyl)-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran
6. ortho-DisubstitutedF-Benzenes. IV. The Formation of 2-Acyl-F-phenyl Carboxylates from (F-Benzo)furans by the Oxidative Cleavage of the Furan-ring [O] . Yoshinari Inukai, Takaaki Sonoda, Hiroshi Kobayashi 1982

机译：Ortho-Disubstitedf-苯并。 IV。通过呋喃环的氧化切割从（F-Benzo）Furans的形成2-酰基-F-苯基羧酸盐

Experimental NMR and DFT Studies of Persistent Carbocations Derived from Hetero-Polycyclic Aromatic Hydrocarbons Containing Oxygen Atom: Dibenzob,dfuran, Benzobnaphtho1,2-dfuran, Benzobnaphtho 2,3-dfuran, Benzobnaphtho 2,1-dfuran, and Dinaphtho2,1-b:1 ',2 '-dfuran

摘要

著录项

相似文献

相关主题

期刊订阅