1H and 13C NMR chemical shifts of 2- n-alkylamino-naphthalene-1,4-diones

Rishikesh Patil; Mahesh Jadhav; Sunita Salunke-Gawali; Dipali N Lande; Shridhar P Gejji; Debamitra Chakravarty

doi:10.1016/j.heliyon.2021.e06044

¹H and ¹³C NMR chemical shifts of 2- n-alkylamino-naphthalene-1,4-diones

Heliyon. 2021 Jan 28;7(1):e06044. doi: 10.1016/j.heliyon.2021.e06044. eCollection 2021 Jan.

Authors

Rishikesh Patil¹, Mahesh Jadhav¹, Sunita Salunke-Gawali¹, Dipali N Lande¹, Shridhar P Gejji¹, Debamitra Chakravarty²

Affiliations

¹ Department of Chemistry, Savitribai Phule Pune University, Pune, 411007, Maharashtra State, India.
² Central Instrumentation Facility, Savitribai Phule Pune University, Pune, 411007, Maharashtra State, India.

Abstract

¹H as well as ¹³C chemical shifts of 32 compounds of C (3) substituted 2-(n-alkylamino)-3R-naphthalene-1,4-dione (where n-alkyl: methyl, to octyl, R = H, Cl, Br, and CH₃) are investigated through ¹H, ¹³C, DEPT, gDQCOSY, and gHSQCAD NMR experiments and M06-2X/6-311++G (d,p) density functional theory are discussed. Single crystal X-ray structure of Br-3, as well as 18 different derivatives of naphthalene-1,4-diones, are revealed for its inter and intra-molecular hydrogen bonding interactions.

Keywords: 2D NMR; Aminonaphthoquinone; Chemical shift; Naphthoquinone.