Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Masahiko Suenaga Last modified date:2021.09.01

Lecturer / Multidisciplinary Chemistry / Department of Chemistry / Faculty of Sciences


Papers
1. Chotika Phupong, Masahiko Suenaga, Phuangthip Bhoopong, Warangkana Chunglok, Gunlanan Jaritngam, Milandip Karak, Keiichi Yoshida, Worrapong Phupong, Kohei Torikai, Precise 1H- and 13C-NMR reassignment of dehydrocrebanine by 10-mg INADEQUATE and in silico analysis: With an alert for its toxicity, Tetrahedron, https://doi.org/10.1016/j.tet.2020.131310, 76, 27, Article 131310, 2020.07.
2. Milandip Karak, Yohei Joh, Masahiko Suenaga, Tohru Oishi, Kohei Torikai, 1,2-trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups
Application to One-Pot Oligosaccharide Synthesis, Organic Letters, 10.1021/acs.orglett.9b00220, 21, 4, 1221-1225, 2019.02, The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides..
3. Masahiko Suenaga, Kazuhide Nakata, José Luis M. Abboud, Masaaki Mishima, A natural bond orbital analysis of aryl-substituted polyfluorinated carbanions
negative hyperconjugation, Journal of Physical Organic Chemistry, 10.1002/poc.3721, 31, 1, 2018.01, Aryl-substituted polyfluorinated carbanions, ArCHRf where Rf = CF3 (1), C2F5 (2), i-C3F7 (3), and t-C4F9 (4), were analyzed by means of the natural bond orbital (NBO) theory at the B3LYP/6-311+G(d,p) computational level. A lone pair NBO at the formal anionic center carbon (Cα) was not found in the Lewis structure. Instead, significant donor/acceptor NBO interactions between π(Cα-C1) and σ*(Cβ-F) or σ*(Cβ-Cγ) were observed for 1, 2, 3a (strong electron-withdrawing substituent, from p-CF3 to p-NO2), and 4. Their second-order donor/acceptor perturbation interaction energy, E(2), values decreased with the increase of the stability of carbanions. A larger E(2) value corresponds to longer Cβ-F and Cβ-Cγ bonds and a shorter Cα-Cβ bond, indicating that the E(2) values can be associated with the negative hyperconjugation of the Cβ-F and Cβ-Cγ bonds. In accordance with this, the E(2) values for π(Cα-C1) → σ*(Cβ-F) were linearly correlated with the ΔGo β-F values (an empirical measure of β-fluorine negative hyperconjugation obtained from an increased acidity). In 3b (weak electron-withdrawing substituents, from H to m-NO2) very large E(2) values for LP(Fβ) → π*(Cα-Cβ) were obtained. This was attributed to the Cβ-F bond cleavage and the Cα-Cβ double bond formation in the Lewis structure that is caused by the extremely strong negative hyperconjugation of the Cβ-F bond..
4. Masahiko Suenaga, Kazuhide Nakata, José Luis M. Abboud, Masaaki Mishima, Negative hyperconjugation in acidity of polyfluorinated alkanes. A natural bond orbital analysis, Bulletin of the Chemical Society of Japan, 10.1246/bcsj.20160353, 90, 3, 289-297, 2017.01, Natural bond orbital (NBO) analysis has been applied to various polyfluorinated carbanions. The E(2)[LP(Cα)→σ∗(Cβ-F) or σ∗(Cβ-Cγ)] values that are interaction energies between a lone pair NBO at the anionic center carbon and the σ∗(Cβ-F) or σ∗(Cβ-Cγ) NBO increased with the corresponding Cβ-F or Cβ-Cγ bond distances, respectively, being consistent with the molecular orbital theory on negative hyperconjugation. The total E(2) values for the interactions of a lone pair orbital with all σ∗(Cβ-F) and σ∗(Cβ-Cγ) orbitals were linearly correlated with gas-phase acidities of the corresponding alkanes, giving two lines for the carbanions having no β-fluorine atom and for the primary and secondary carbanions having β-fluorine atoms (slopes of 0.57 and 1.56, respectively). The major E(2)[LP(Cα)→σ∗(Cβ-F)] values in the respective anions were found to be linearly correlated with the ΔG°β-F values as an empirical measure of β-fluorine negative hyperconjugation obtained from an increased acidity of the molecule owing to the presence of β-fluorine. However, the magnitude of ΔG°β-F was much smaller than the E(2)[LP(Cα)→σ∗(Cβ-F)] value, indicating that the absolute values of the β-fluorine negative hyperconjugation are smaller than the E(2) interaction energies..
5. Masaaki Mishima, José-Luis M. Abboud, Mizue Fujio, Masahiko Suenaga, Heinz F. Koch, Judith G. Koch, Gas-phase Acidities of 2-Aryl-2-chloro-1,1,1-trifluoroethanes and Related Compounds.
Experimental and Computational Studies, 10.1002/poc.3576, 29, 523-531, 2016.05, The gas-phase acidities (GA) of 2-aryl-2-chloro-1,1,1-trifluoroethanes (1a), 2-aryl-2-fluoro-1,1,1-trifluoroethanes (2a), and related compounds, XC6H4CH(Z)R where Z = Cl (1) or F (2) and R = C2F5 (b), t-C4F9 (c), C(CF3)2C2F5 (d), C(CF3)2Me (e), Me (f),H (g), were investigated experimentally and computationally. On the basis of an excellent linear correlation (R2>0.99) of acidities of 1c-f and 2c-f where there is no fluorine atom at β-position to the deprotonation site with the corrected number of fluorine atoms contained in the fluorinated alkyl group, the extent of β-fluorine negative hyperconjugation of the CF3 and C2F5 groups (ΔGoβ-F) was evaluated. The GAel values given by subtraction ΔGoβ-F from the apparent GA value were considered to represent the electronic effect of the substituent X. The substituent effects on the GAel values and GA values for 1c-f and 2c-f were successfully analyzed in terms of the Yukawa–Tsuno equation. The variation of resonance demand parameter r with the R group observed for various XC6H4CH(Z)R was linearly related to the GA (GAel) value of the respective phenylsubstituted
fluorinated alkanes. On the other hand, the corresponding correlation for the ρ values provided three lines
for ArCH(Cl)R, ArCH(F)R and ArCH2R, respectively. These results supported our previous conclusion that the r and ρ values are governed by the thermodynamic stability of the parent ion (ring substituent = H). Other factors arising from an atom bonded to the acidic center also influence the ρ value..
6. Mariappan Mariappan, Masahiko Suenaga, Abhik Mukhopadhyay, Pallepogu Raghavaih, and Bhaskar G. Maiya, Synthesis, structure, DNA binding and photocleavage activity of a ruthenium(II) complex with 11-(9-acridinyl)dipyrido[3,2-a:2',3'-c]phenazine ligand, Inorganica Chimica Acta, 10.1016, 376, 340, 2011.08.
7. Kikuko Hayamizu, Seiji Tsuzuki, Shiro Seki, Kenta Fujii, Masahiko Suenaga, and Yasuhiro Umebayashi, Studies on the translational and rotational motions of ionic liquids composed of N-methyl-N-propyl-pyrrolidinium (P13) cation and bis(trifluoromethanesulfonyl)amide and bis(fluorosulfonyl)amide anions and their binary systems including lithium salts, The Journal of Chemical Physics, 133, 194505, 2010.11.
8. M. Shibahara, M. Watanabe, M. Suenaga, K. Ideta, T. Matsumoto, and T. Shinmyozu, A Conformational Study of [3.3](3,5)Pyridinophane, Tetrahedron Letters, 50, 1340, 2009.03.
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11. Facio: New Computational Chemistry Environment for PC GAMESS
M. Suenaga, Journal of Computer Chemistry, Japan, Vol. 4, No. 1 pp. 25-32 (2005).
12. The Model Of A Supermolecule With Dodecahedral Symmetry
M. Suenaga, Journal of Computer Chemistry, Japan, Vol. 3, No. 1 pp.27-34 (2004).
13. Development Of A Server/Client Type Reagent Management System (Servo) Using PostgreSQL As A Database
M. Suenaga, Journal of Computer Chemistry, Japan, Vol. 2, No. 1 pp.41-48 (2003).
14. Y. Miyahara, Y. Tanaka, K. Amimoto, T. Akazawa, T. Sakuragi, H. Kobayashi, K. Kubota, M. Suenaga, H. Koyama, and T. Inazu, The Proton Cryptate of Hexaethylenetetramine, Angew. Chem. Int. Ed., 10.1002/(SICI)1521-3773(19990401)38:7<956::AID-ANIE956>3.3.CO;2-B, 38, 7, 956-959, 38, 956-959 (1999), 1999.04.
15. A. A. Ibrahim, M. Matsumoto, Y. Miyahara, K. Izumi, M. Suenaga, N. Shimizu, and T. Inazu, Synthesis and Properties of a New Series of Troegaropnanes, J. Heterocyclic Chem., 35, 1, 209-215, 35, 209-215 (1998), 1998.01.
16. M. Suenaga, Y. Miyahara, N. Shimizu, and T. Inazu, Synthesis of the Trinaphthophenalenium Cation, Angew. Chem. Int. Ed., 10.1002/(SICI)1521-3773(19980202)37:1/2<90::AID-ANIE90>3.3.CO;2-7, 37, 1-2, 90-91, 37, 90-91 (1998), 1998.01.
17. M. Suenaga, Y. Miyahara, and T. Inazu, A Novel Approach to Extended Phenalenones, J. Org. Chem., 10.1021/jo00073a054, 58, 21, 5846-5848, 58, 5846-5848 (1993), 1993.07.
18. I. U. Khan, H. Takemura, M. Suenaga, T. Shinmozu, and T. Inazu, Azacalixarenes: New Macrocycles with Dimethyleneaza-Bridged Calix[4]arene Systems, J. Org. Chem., 10.1021/jo00063a042, 58, 11, 3158-3161, 58, 3158-3168 (1993), 1993.07.
19. K. Sako, T. Shinmyozu, H. Takemura, M. Suenaga, and T. Inazu, A Conformational Study of [3.3]Metacyclophanes Through Variable
Temperature 1H NMR and Optical Rotation, J. Org. Chem., 10.1021/jo00050a031, 57, 24, 6536-6541, 57, 6536-6541 (1992), 1992.09.
20. T. Meno, K. Sako, M. Suenaga, M. Mouri, T. Shinmyozu, and T. Inazu, Conformational Analysis of [3.3.3](1,3,5)Cyclophane Systems, Can. J. Chem., 10.1139/v90-067, 68, 3, 440-445, 68, 440-445. (1990), 1990.02.
21. H. Takemura, M. Suenaga, K. Sakai, H. Kawachi, T. Shinmyozu, Y. Miyahara, and T. Inazu, Synthesis of (Aza)n[3n]Cyclophanes As Host Molecules, Journal of Inclusion Phenomena, 2, 207-214 (1984), 1984.03.
22. K. Kurosawa, M. Suenaga, T. Inazu, and T. Yoshino, A Facile Synthesis of [3n]Cyclophanes, in which Aromatic
Rings Are Connected With -CH2-CO-CH2- Bridges, Tetrahedron Letters, 10.1016/S0040-4039(00)85832-3, 23, 50, 5335-5338, Tetrahedron Lett., 23, 5335-5338 (1982), 1982.06.