《Influence of Substituents in the Aromatic Ring on the Strength of Halogen Bonding in Iodobenzene Derivatives》 was written by Chernysheva, Maria V.; Bulatova, Margarita; Ding, Xin; Haukka, Matti. Name: 3-Iodophenol And the article was included in Crystal Growth & Design in 2020. The article conveys some information:
The halogen-bonding properties of 3,4,5-triiodobenzoic acid (1, 2), 1,2,3-triiodobenzene (3), 4-iodobenzoic acid (4), pentaiodobenzoic acid ethanol solvate (5), hexaiodobenzene (6a-c), 4-iodobenzonitrile (7), 3-iodobenzonitrile (8), 2,4-diiodoaniline (9), 4-iodoaniline (10), 2-iodoaniline (11), 2-iodophenol (12), 4-iodophenol (13), 3-iodophenol (14), 2,4,6-triiodophenol (15), 4-iodoanisole (16), and 3,4,5-triiodoanisole (17) have been studied. The results suggested that substituents other than halogen in the aromatic ring affect the XB properties of iodide substituents in ortho, meta, and para positions. The effect depends on the electron-withdrawing/electron-donating properties of the substituent. Thus, electron-donating substituents with a pos. mesomeric effect favor m-iodines to act as XB donors. In contrast, electron substituents with a neg. mesomeric effect favor o- and p-iodines to act as XB donors. Furthermore, the stronger the mesomeric effect of the EWG or EDG substituent, the higher the effect it has on the size of the σ-hole and, consequently, on the XB donor ability of the iodide substituent. Structural and computational MEP analyses of 3,4,5-triiodobenzoic acid (1, 2), 1,2,3-triiodobenzene (3), 4-iodobenzoic acid (4), pentaiodobenzoic acid ethanol solvate (5), hexaiodobenzene (6a-c), 4-iodobenzonitrile (7), 3-iodobenzonitrile (8), 2,4-diiodoaniline (9), 4-iodoaniline (10), 2-iodoaniline (11), 2-iodophenol (12), 4-iodophenol (13), 3-iodophenol (14), 2,4,6-triiodophenol (15), 4-iodoanisole (16), and 3,4,5-triiodoanisole (17) have been conducted. The results show that the mesomeric effect of the substituents other than halogen in the benzene ring has an effect on the XB donor-acceptor properties of the iodide substituents in ortho, meta, and para positions. Thus, electron-withdrawing (EWG) substituents with a neg. mesomeric effect, e.g. carboxyl (-COOH) and nitrile (-CN), favor iodines in ortho and para positions to act as halogen-bond donors. On the other hand, electron-donating (EDG) substituents, such as amino (-NH2), hydroxy (-OH), and methoxy (-OCH3) groups, which have a pos. mesomeric effect, increase the ability of m-iodines to act as halogen bond donors. Furthermore, EWG and EDG substituents with stronger mesomeric effects have a greater effect on the XB donor ability of the iodide substituents. Such a correlation is reflected in the size of the σ hole on the iodine atoms. Thus, the σ holes on o- and p-iodine atoms are larger than on m-iodine atoms in the presence of an EWG, making o- and p-iodines favorable XB donors. Similarly, the size of the σ hole on m-iodines is larger than those on o- and p-iodines in the presence of an EDG, causing m-iodines to favor XB donor behavior. This is confirmed by our MEP calculations, in which the size of the σ hole is expressed by the value of the maximum electrostatic potential (VS,max), being a maximum in the case of strong EWG substituents and a min. in the case of strong EDG substituents.3-Iodophenol(cas: 626-02-8Name: 3-Iodophenol) was used in this study.
3-Iodophenol(cas: 626-02-8) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Name: 3-Iodophenol
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com