Araştırma Makalesi
BibTex RIS Kaynak Göster

Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate

Yıl 2023, Cilt: 7 Sayı: 2, 72 - 78, 31.12.2023

Hasan İnaç

https://doi.org/10.47897/bilmes.1316337

Öz

The title compound (1), C19H20N2O2, crystallized with single molecule in the asymmetric unit and is present in the zwitterionic form. The compound was synthesized from the condensation reaction of 8-hydroxyjulolidine-9-carbaldehyde and 3-aminophenol. In solid state compound adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H···O hydrogen bond with an S(6) ring motif. The conformation about the C=N bond is E. The aromatic ring of the julolidine moiety is inclined to the phenol ring by 13.00 (10)°. The fused non-aromatic rings of the julolidine moiety adopts a screw-boat conformations. In the crystal, the molecules are connected by N—H···O and O—H···O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating– A–B–A–B–zigzag chains extending along [010]. Furthermore, adjacent molecules are linked by pairs of C—H···O interactions, forming a ladder-like structure propagating along the a-axis direction. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

Anahtar Kelimeler

Crystal structure schiff base julolidine 8-hydroxyjulolidine-9-carboxaldehyde hydrogen bonding zwitterion 3-aminophenol

Kaynakça

  • [1] Narayanaswamy, N. & Govindaraju, T. (2012). “Sens. Actuators B”, Chem. 161, 304–310.
  • [2] Maity, D., Manna, A. K., Karthigeyan, D., Kundu, T. K., Pati, S. K. & Govindaraju, T. (2011). “Chem. Eur. J”. 17, 11152–11161.
  • [3] Noh, J. Y., Kim, S., Hwang, I. H., Lee, G. Y., Kang, J., Kim, S. H., Min, J., Park, S., Kim, C. & Kim, J. (2013). “Dyes Pigments”, 99, 1016–1021.
  • [4] Nano, A., Gullo, M. P., Ventura, B., Armaroli, N., Barbieri, A. & Ziessel, R. (2015). “Chem. Commun”.51, 3351–3354.
  • [5] Jo, T. G., Na, Y. J., Lee, J. J., Lee, M. M., Lee, S. Y. & Kim, C. (2015). “New J. Chem”. 39, 2580–2587.
  • [6] Choi, Y. W., Lee, J. J., You, G. R., Lee, S. Y. & Kim, C. (2015). “RSC Adv”. 5, 86463–86472.
  • [7] Kim, Y. S., Lee, J. J., Choi, Y. W., You, G. R., Nguyen, L., Noh, I. & Kim, C. (2016). “Dyes Pigments”, 129, 43–53.
  • [8] Lee, S. A., You, G. R., Choi, Y. W., Jo, H. Y., Kim, A. R., Noh, I., Kim, S.-J., Kim, Y. & Kim, C. (2014). “Dalton Trans.” 43, 6650–6659.
  • [9] Mennucci, B., Cappelli, C., Guido, C. A., Cammi, R. & Tomasi, J. (2009). “J. Phys. Chem. A”, 113, 3009–3020.
  • [10] Park, G. J., Park, D. Y., Park, K.-M., Kim, Y., Kim, S.-J., Chang, P.-S. & Kim, C. (2014). “Tetrahedron”, 70, 7429–7438.
  • [11] Faizi, M. S. H., Ali, A. & Potaskalov, V. A. (2016). “Acta Cryst”. E72, 1366–1369.
  • [12] Faizi, M. S. H., Ahmad, M., Kapshuk, A. A. & Golenya, I. A. (2017a). “Acta Cryst”. E73,38–40
  • [13] Faizi, M. S. H., Dege, N. & Malysheva, M. L. (2017b). “Acta Cryst”. E73, 791–794.
  • [14] Na, Y. J., Hwang, I. H., Jo, H. Y., Lee, S. A., Park, G. J. & Kim, C. (2013). Inorg. “Chem. Commun”. 35, 342–345.
  • [15] Faizi, M. S. H., Iskenderov, T. S. & Sharkina, N. O. (2015). “Acta Cryst”. E71, 28–30.
  • [16] Kantar, E. N., Köysal, Y., Akdemir, N., Agăr, A. A. & Soylu, M. S. (2013). “Acta Cryst”. E69,0883
  • [17] Frisch, M. J., et al. (2009). GAUSSIAN09. Revision A. 02. Gaussian Inc., Wallingford, CT, USA.
  • [18] Becke, A. D. (1993). “J. Chem. Phys”. 98, 5648–5652.
  • [19] Groom (2016). “The cabricke structural data base”. Acta crystallographice B,72,171-179

Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate

Yıl 2023, Cilt: 7 Sayı: 2, 72 - 78, 31.12.2023

Hasan İnaç

https://doi.org/10.47897/bilmes.1316337

Öz

The title compound (1), C19H20N2O2, crystallized with single molecule in the asymmetric unit and is present in the zwitterionic form. The compound was synthesized from the condensation reaction of 8-hydroxyjulolidine-9-carbaldehyde and 3-aminophenol. In solid state compound adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N—H···O hydrogen bond with an S(6) ring motif. The conformation about the C=N bond is E. The aromatic ring of the julolidine moiety is inclined to the phenol ring by 13.00 (10)°. The fused non-aromatic rings of the julolidine moiety adopts a screw-boat conformations. In the crystal, the molecules are connected by N—H···O and O—H···O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating– A–B–A–B–zigzag chains extending along [010]. Furthermore, adjacent molecules are linked by pairs of C—H···O interactions, forming a ladder-like structure propagating along the a-axis direction. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

Anahtar Kelimeler

Crystal structure schiff base julolidine 8-hydroxyjulolidine-9-carboxaldehyde hydrogen bonding zwitterion 3-aminophenol

Kaynakça

  • [1] Narayanaswamy, N. & Govindaraju, T. (2012). “Sens. Actuators B”, Chem. 161, 304–310.
  • [2] Maity, D., Manna, A. K., Karthigeyan, D., Kundu, T. K., Pati, S. K. & Govindaraju, T. (2011). “Chem. Eur. J”. 17, 11152–11161.
  • [3] Noh, J. Y., Kim, S., Hwang, I. H., Lee, G. Y., Kang, J., Kim, S. H., Min, J., Park, S., Kim, C. & Kim, J. (2013). “Dyes Pigments”, 99, 1016–1021.
  • [4] Nano, A., Gullo, M. P., Ventura, B., Armaroli, N., Barbieri, A. & Ziessel, R. (2015). “Chem. Commun”.51, 3351–3354.
  • [5] Jo, T. G., Na, Y. J., Lee, J. J., Lee, M. M., Lee, S. Y. & Kim, C. (2015). “New J. Chem”. 39, 2580–2587.
  • [6] Choi, Y. W., Lee, J. J., You, G. R., Lee, S. Y. & Kim, C. (2015). “RSC Adv”. 5, 86463–86472.
  • [7] Kim, Y. S., Lee, J. J., Choi, Y. W., You, G. R., Nguyen, L., Noh, I. & Kim, C. (2016). “Dyes Pigments”, 129, 43–53.
  • [8] Lee, S. A., You, G. R., Choi, Y. W., Jo, H. Y., Kim, A. R., Noh, I., Kim, S.-J., Kim, Y. & Kim, C. (2014). “Dalton Trans.” 43, 6650–6659.
  • [9] Mennucci, B., Cappelli, C., Guido, C. A., Cammi, R. & Tomasi, J. (2009). “J. Phys. Chem. A”, 113, 3009–3020.
  • [10] Park, G. J., Park, D. Y., Park, K.-M., Kim, Y., Kim, S.-J., Chang, P.-S. & Kim, C. (2014). “Tetrahedron”, 70, 7429–7438.
  • [11] Faizi, M. S. H., Ali, A. & Potaskalov, V. A. (2016). “Acta Cryst”. E72, 1366–1369.
  • [12] Faizi, M. S. H., Ahmad, M., Kapshuk, A. A. & Golenya, I. A. (2017a). “Acta Cryst”. E73,38–40
  • [13] Faizi, M. S. H., Dege, N. & Malysheva, M. L. (2017b). “Acta Cryst”. E73, 791–794.
  • [14] Na, Y. J., Hwang, I. H., Jo, H. Y., Lee, S. A., Park, G. J. & Kim, C. (2013). Inorg. “Chem. Commun”. 35, 342–345.
  • [15] Faizi, M. S. H., Iskenderov, T. S. & Sharkina, N. O. (2015). “Acta Cryst”. E71, 28–30.
  • [16] Kantar, E. N., Köysal, Y., Akdemir, N., Agăr, A. A. & Soylu, M. S. (2013). “Acta Cryst”. E69,0883
  • [17] Frisch, M. J., et al. (2009). GAUSSIAN09. Revision A. 02. Gaussian Inc., Wallingford, CT, USA.
  • [18] Becke, A. D. (1993). “J. Chem. Phys”. 98, 5648–5652.
  • [19] Groom (2016). “The cabricke structural data base”. Acta crystallographice B,72,171-179
Toplam 19 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Atom ve Molekül Fiziği, Malzeme Fiziği
Bölüm Makaleler
Yazarlar

Hasan İnaç 0000-0002-8870-5317

Yayımlanma Tarihi 31 Aralık 2023
Kabul Tarihi 14 Ağustos 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 7 Sayı: 2

Kaynak Göster

APA İnaç, H. (2023). Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. International Scientific and Vocational Studies Journal, 7(2), 72-78. https://doi.org/10.47897/bilmes.1316337
AMA İnaç H. Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. ISVOS. Aralık 2023;7(2):72-78. doi:10.47897/bilmes.1316337
Chicago İnaç, Hasan. “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”. International Scientific and Vocational Studies Journal 7, sy. 2 (Aralık 2023): 72-78. https://doi.org/10.47897/bilmes.1316337.
EndNote İnaç H (01 Aralık 2023) Crystal Structure of Zwitterionic (E)-9-(3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. International Scientific and Vocational Studies Journal 7 2 72–78.
IEEE H. İnaç, “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”, ISVOS, c. 7, sy. 2, ss. 72–78, 2023, doi: 10.47897/bilmes.1316337.
ISNAD İnaç, Hasan. “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”. International Scientific and Vocational Studies Journal 7/2 (Aralık 2023), 72-78. https://doi.org/10.47897/bilmes.1316337.
JAMA İnaç H. Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. ISVOS. 2023;7:72–78.
MLA İnaç, Hasan. “Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate”. International Scientific and Vocational Studies Journal, c. 7, sy. 2, 2023, ss. 72-78, doi:10.47897/bilmes.1316337.
Vancouver İnaç H. Crystal Structure of Zwitterionic (E)-9-(((3-hydroxyphenyl)iminio)methyl)-1,2,3,5,6,7- Hexahydropyrido[3,2,1-ij]Quinolin-8-Olate. ISVOS. 2023;7(2):72-8.
 Kapak Resmi İndir


Creative Commons License
Creative Commons Atıf 4.0 It is licensed under an International License