Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction: their characterization and DFT studies

Komal Rizwan; Nasir Rasool; Ravya Rehman; Tariq Mahmood; Khurshid Ayub; Tahir Rasheed; Gulraiz Ahmad; Ayesha Malik; Shakeel Ahmad Khan; Muhammad Nadeem Akhtar; Noorjahan Banu Alitheen; Muhammad Nazirul Mubin Aziz

doi:10.1186/s13065-018-0451-0

Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction: their characterization and DFT studies

Komal Rizwan, Nasir Rasool^*, Ravya Rehman, Tariq Mahmood, Khurshid Ayub, Tahir Rasheed, Gulraiz Ahmad, Ayesha Malik, Shakeel Ahmad Khan, Muhammad Nadeem Akhtar, Noorjahan Banu Alitheen, Muhammad Nazirul Mubin Aziz

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

A variety of imine derivatives have been synthesized via Suzuki cross coupling of N-(4-bromophenyl)-1-(3-bromothiophen-2-yl)methanimine with various arylboronic acids in moderate to good yields (58–72%). A wide range of electron donating and withdrawing functional groups were well tolerated in reaction conditions. To explore the structural properties, Density functional theory (DFT) investigations on all synthesized molecules (3a–3i) were performed. Conceptual DFT reactivity descriptors and molecular electrostatic potential analyses were performed by using B3LYP/6-31G(d,p) method to explore the reactivity and reacting sites of all derivatives (3a–3i).

Original language	English
Article number	84
Journal	Chemistry Central Journal
Volume	12
Issue number	1
DOIs	https://doi.org/10.1186/s13065-018-0451-0
State	Published - 1 Dec 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018, The Author(s).

Keywords

Computational
Density functional theory
Imines
Reactivity
Suzuki coupling
Thiophene

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1186/s13065-018-0451-0

Cite this

Rizwan, K., Rasool, N., Rehman, R., Mahmood, T., Ayub, K., Rasheed, T., Ahmad, G., Malik, A., Khan, S. A., Akhtar, M. N., Alitheen, N. B., & Aziz, M. N. M. (2018). Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction: their characterization and DFT studies. Chemistry Central Journal, 12(1), Article 84. https://doi.org/10.1186/s13065-018-0451-0

@article{e7660787e1254a60ac9b77b36ebab5e0,

title = "Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction: their characterization and DFT studies",

abstract = "A variety of imine derivatives have been synthesized via Suzuki cross coupling of N-(4-bromophenyl)-1-(3-bromothiophen-2-yl)methanimine with various arylboronic acids in moderate to good yields (58–72%). A wide range of electron donating and withdrawing functional groups were well tolerated in reaction conditions. To explore the structural properties, Density functional theory (DFT) investigations on all synthesized molecules (3a–3i) were performed. Conceptual DFT reactivity descriptors and molecular electrostatic potential analyses were performed by using B3LYP/6-31G(d,p) method to explore the reactivity and reacting sites of all derivatives (3a–3i).",

keywords = "Computational, Density functional theory, Imines, Reactivity, Suzuki coupling, Thiophene",

author = "Komal Rizwan and Nasir Rasool and Ravya Rehman and Tariq Mahmood and Khurshid Ayub and Tahir Rasheed and Gulraiz Ahmad and Ayesha Malik and Khan, {Shakeel Ahmad} and Akhtar, {Muhammad Nadeem} and Alitheen, {Noorjahan Banu} and Aziz, {Muhammad Nazirul Mubin}",

note = "Publisher Copyright: {\textcopyright} 2018, The Author(s).",

year = "2018",

month = dec,

day = "1",

doi = "10.1186/s13065-018-0451-0",

language = "English",

volume = "12",

journal = "Chemistry Central Journal",

issn = "1752-153X",

publisher = "Chemistry Central",

number = "1",

}

Rizwan, K, Rasool, N, Rehman, R, Mahmood, T, Ayub, K, Rasheed, T, Ahmad, G, Malik, A, Khan, SA, Akhtar, MN, Alitheen, NB & Aziz, MNM 2018, 'Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction: their characterization and DFT studies', Chemistry Central Journal, vol. 12, no. 1, 84. https://doi.org/10.1186/s13065-018-0451-0

TY - JOUR

T1 - Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction

T2 - their characterization and DFT studies

AU - Rizwan, Komal

AU - Rasool, Nasir

AU - Rehman, Ravya

AU - Mahmood, Tariq

AU - Ayub, Khurshid

AU - Rasheed, Tahir

AU - Ahmad, Gulraiz

AU - Malik, Ayesha

AU - Khan, Shakeel Ahmad

AU - Akhtar, Muhammad Nadeem

AU - Alitheen, Noorjahan Banu

AU - Aziz, Muhammad Nazirul Mubin

PY - 2018/12/1

Y1 - 2018/12/1

N2 - A variety of imine derivatives have been synthesized via Suzuki cross coupling of N-(4-bromophenyl)-1-(3-bromothiophen-2-yl)methanimine with various arylboronic acids in moderate to good yields (58–72%). A wide range of electron donating and withdrawing functional groups were well tolerated in reaction conditions. To explore the structural properties, Density functional theory (DFT) investigations on all synthesized molecules (3a–3i) were performed. Conceptual DFT reactivity descriptors and molecular electrostatic potential analyses were performed by using B3LYP/6-31G(d,p) method to explore the reactivity and reacting sites of all derivatives (3a–3i).

AB - A variety of imine derivatives have been synthesized via Suzuki cross coupling of N-(4-bromophenyl)-1-(3-bromothiophen-2-yl)methanimine with various arylboronic acids in moderate to good yields (58–72%). A wide range of electron donating and withdrawing functional groups were well tolerated in reaction conditions. To explore the structural properties, Density functional theory (DFT) investigations on all synthesized molecules (3a–3i) were performed. Conceptual DFT reactivity descriptors and molecular electrostatic potential analyses were performed by using B3LYP/6-31G(d,p) method to explore the reactivity and reacting sites of all derivatives (3a–3i).

KW - Computational

KW - Density functional theory

KW - Imines

KW - Reactivity

KW - Suzuki coupling

KW - Thiophene

UR - http://www.scopus.com/inward/record.url?scp=85050227594&partnerID=8YFLogxK

U2 - 10.1186/s13065-018-0451-0

DO - 10.1186/s13065-018-0451-0

M3 - Article

AN - SCOPUS:85050227594

SN - 1752-153X

VL - 12

JO - Chemistry Central Journal

JF - Chemistry Central Journal

IS - 1

M1 - 84

ER -

Facile synthesis of N- (4-bromophenyl)-1- (3-bromothiophen-2-yl)methanimine derivatives via Suzuki cross-coupling reaction: their characterization and DFT studies

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this