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Synthesis and Crystal Structures of the Derivatives of Butyrate and 1,3-Dioxane; Allyl 2-acetyl-3-(phenylamino)butanoate, 2,6-Dimethyl N-(4-methylphenyl)-1,3-dioxan-4-amine and N-(3,5-Diflourophenyl)-2,6-dimethyl-1,3-dioxan-4-amine

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Abstract

Butyrate derivatives of allyl 2-acetyl-3-(phenylamino)butanoate (1) and 1,3-dioxane derivatives of 2,6-dimethyl N-(4-methylphenyl)-1,3-dioxan-4-amine (2) and N-(3,5-diflourophenyl)-2,6-dimethyl-1,3-dioxan-4-amine (3) were synthesised. Their structures were characterized by FTIR (1) 1H NMR, 13C NMR spectroscopic techniques and single crystal X-ray diffraction. The compound (1) crystallizes in the triclinic crystal system with the space group p-1 with a = 10.0874(5) Å, b = 10.1751(5) Å, c = 14.1930(8) Å, α = 82.429(4)°, β = 77.482(4)°, γ = 80.820(4)°, v = 1396.77(13) Å3. The compound (2) crystallizes in the monoclinic space group P21/C with unit cell dimensions a = 9.8454(3) Å, b = 13.3032(4) Å, c = 10.1967(3) Å, α = 90°, β = 114.821(2)°, γ = 90°, v = 1212.15(6) Å3. The compound (3) crystallizes in the triclinic space group p-1 with unit cell dimensions a = 9.65630(10) Å, b = 11.2266(2) Å, c = 11.2658(2) Å, α = 83.7710(10)°, β = 79.1770(10)°, γ = 77.1290(10)°, v = 1166.59(3) Å3.

Graphical Abstract

In the crystal packing of all the three crystal structures, the molecules are linked together by hydrogen bonds to form dimers.

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Acknowledgments

The authors extend their appreciation to The Deanship of Scientific Research at King Saud University for the funding the work through the research group project No. RGP-VPP-207.

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Authors and Affiliations

  1. Department of Physics, Sethupathy Government Arts College, Ramanathapuram, 623502, India

    Samuel Robinson Jebas

  2. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, 11451, Kingdom of Saudi Arabia

    Hoong-Kun Fun

  3. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Georgetown, Penang, Malaysia

    Hoong-Kun Fun, Ching Kheng Quah & Chin Wei Ooi

  4. Chemistry Department, GEBH, Sree Vidyanikethan Engineering College, A. Rangampet, Tirupati, 517102, India

    Gottimukkala Rambabu

  5. Centre for Organic and Medicinal Chemistry, VIT University, Vellore, 632014, India

    Vijayaparthasarathi Vijayakumar & Sundaramoorthy Sarveswari

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  1. Samuel Robinson Jebas
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Correspondence to Hoong-Kun Fun.

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Jebas, S.R., Fun, HK., Quah, C.K. et al. Synthesis and Crystal Structures of the Derivatives of Butyrate and 1,3-Dioxane; Allyl 2-acetyl-3-(phenylamino)butanoate, 2,6-Dimethyl N-(4-methylphenyl)-1,3-dioxan-4-amine and N-(3,5-Diflourophenyl)-2,6-dimethyl-1,3-dioxan-4-amine. J Chem Crystallogr 43, 523–530 (2013). https://doi.org/10.1007/s10870-013-0452-8

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