Using Data Analysis To Evaluate and Compare Chemical Syntheses

We present ChemPager, a freely available tool for systematically evaluating chemical syntheses. By processing and visualizing chemical data, the impact of past changes is uncovered and future work guided. The tool calculates commonly used metrics such as process mass intensity (PMI), Volume–Time Output, and production costs. Also, a set of scores is introduced aiming to measure crucial but elusive characteristics such as process robustness, design, and safety. Our tool employs a hierarchical data layout built on common software for data entry (Excel, Google Sheets, etc.) and visualization (Spotfire). With all project data being stored in one place, cross-project comparison and data aggregation becomes possible as well as cross-linking with other data sources or visualizations

Using Data Analysis To Evaluate and Compare Chemical Syntheses

We present ChemPager, a freely available tool for systematically evaluating chemical syntheses. By processing and visualizing chemical data, the impact of past changes is uncovered and future work guided. The tool calculates commonly used metrics such as process mass intensity (PMI), Volume–Time Output, and production costs. Also, a set of scores is introduced aiming to measure crucial but elusive characteristics such as process robustness, design, and safety. Our tool employs a hierarchical data layout built on common software for data entry (Excel, Google Sheets, etc.) and visualization (Spotfire). With all project data being stored in one place, cross-project comparison and data aggregation becomes possible as well as cross-linking with other data sources or visualizations

Using Data Analysis To Evaluate and Compare Chemical Syntheses

We present ChemPager, a freely available tool for systematically evaluating chemical syntheses. By processing and visualizing chemical data, the impact of past changes is uncovered and future work guided. The tool calculates commonly used metrics such as process mass intensity (PMI), Volume–Time Output, and production costs. Also, a set of scores is introduced aiming to measure crucial but elusive characteristics such as process robustness, design, and safety. Our tool employs a hierarchical data layout built on common software for data entry (Excel, Google Sheets, etc.) and visualization (Spotfire). With all project data being stored in one place, cross-project comparison and data aggregation becomes possible as well as cross-linking with other data sources or visualizations

Mechanistical Insights into the Bioconjugation Reaction of Triazolinediones with Tyrosine

The bioconjugation at tyrosine residues using cyclic diazodicarboxamides, especially 4-substituted 3<i>H</i>-1,2,4-triazole-3,5­(4<i>H</i>)-dione (PTAD), is a highly enabling synthetic reaction because it can be employed for orthogonal and site-selective (multi)­functionalizations of native peptides and proteins. Despite its importance, the underlying mechanisms have not been thoroughly investigated. The reaction can proceed along four distinctive pathways: (i) the S_EAr path, (ii) along a pericyclic group transfer pathway (a classical ene reaction), (iii) along a stepwise reaction path, or (iv) along an unusual higher order concerted pericyclic mechanism. The product mixtures obtained from reactions of PTAD with 2,4-unsubstituted phenolate support the S_EAr mechanism, but it remains unclear if other mechanisms also take place. In the present work, the various mechanisms are compared using high-level quantum chemistry approaches for the model reaction of 4<i>H</i>,3<i>H</i>-1,2,4-triazole-3,5­(4<i>H</i>)-dione (HTAD) with <i>p</i>-cresol and <i>p</i>-cresolate. In a protic solvent (water), the barriers of the S_EAr mechanism and the ene reaction are similar but still too high to explain the available experimental observations. This is only possible if the S_EAr reaction of cresolate with HTAD is taken into account for which nearly vanishing barriers are computed. This satisfactorily explains measured conversion rates in buffered aqueous solutions and the strong activation effects observed upon addition of bases